Gulopyranoside, methyl 6-deoxy

A mixture of d- and l- hexoses also results from the hydroboration of these 5-enes. Hydroboration results in anti-Markownikoff, cw-hydration of the double bond and the amount of each hexose formed varies according to the nature of the substituent groups. For example, hydroboration (23) of methyl 6-deoxy-a-D-ryZo-hex-5-enopyranose (3) affords methyl a-D-glucopyranoside and methyl / -L-idopyranoside in the ratio of 1 2.5 respectively whereas hydroboration of the fris-trimethylsilyl ether of 3 afforded them in the ratio 1 0.6 respectively. The hydroboration method can be used to achieve specific labelling of hexoses with tritium methyl-/ -L-idopyranoside[5-H3] and methyl a-D-glucopyranoside [5-H3] were thus prepared (23). Similarly, hydroboration of the D-Zt/ro-hex-5-eno derivative (14) with diborane-H3 followed by removal of the isopropyli-dene group, afforded methyl a-D-mannopyranoside [5-H3] and methyl / -L-gulopyranoside [5-H3] in the ratio of 1 2 respectively (23). 

Methyl 6-deoxy- 2,3-0-isopropylidene-a-D-gulopyranoside (lOg) Methyl 6-deoxy-2,3-0-isopropylidene-a-D-n7)o-hexopyranosid-4-ulose G [333]... 

A similar orientation was found for the bromination of methyl 3,4-0-benzylidene-6-deoxy-/3-D-fucopyranoside (101), which gave135 methyl 4-0-benzoyl-3-bromo-3,6-dideoxy-D-gulopyranoside (102). It appears... 

C31H31BrN2O10 3-(4-Bromobenzamido)-4-hydroxy-8-methyl-7-[3-0-(5-methyl-2-pyrrolylcarbonyl)noviopyranosyloxy]coumarin71 P212l2I Z = 4 Dx = 1.448 R = 0.047 for 1,568 intensities. This compound is a 6-deoxy-6-methy 1-a-D-gulopyranoside, related to the antibiotics coumermycin A and novobiocin. The pyranosyl residue is in... 

Boigegrain, R A, Gross, B, Syntheses in the 6-deoxy-4-thiohexose series. II. S3mthesis of methyl 3,4, 6-trideoxy-3,4-epithio-2-0-methylsulfonyl-a-D-allopyranoside and l,2,3-tri-0-acetyl-4-S-acetyl-6-deoxy-4-thio-a- and (3-D-gulopyranosides, Carbohydr. Res., 41, 135-142, 1975. 

An alternative, or supplementary, approach is provided by oxidation with lead tetraacetate or, preferably, periodate, and possibly by identification of the products. Caution must, however, be observed in using this method, as Buchanan has shown that the compound previously designated as methyl 3-chloro-3-deoxy-a-D-gulopyranoside consumes periodic acid extremely slowly (seven days) and is, in fact, methyl 4-chloro-4-deoxy-a-D-glucopyranoside. The products of epoxide cleavage are usually completely defined by these procedures, because irans addition can be assumed, although considerable care must be exercised when there is a possibility of epoxide migration. ... 

Methanolysis of the anti-tumour antibiotic virenomycin afforded methyl 6-deoxy-3-C-methyl- 3-D-gulopyranoside (1), the structure of which was indicated by a combination of periodate oxidation and spectroscopic studies. ... 

Another new anti-tumour antibiotic, virenomycin A, has the branched-chain sugar 6-deoxy-3-C-methyl-D-gulopyranoside (37) -linked as a C-glycoside to the same aglycone present in gilvocarcin V and ravidomycin (see Vol.17,p.181,182). 

Me glycoside, N-Ac Methyl 2-acetarrudo-2-deoxy-a-D-gulopyranoside CsHiyNO 235.236 Mp 79-82°. [a] +72 (c, 0.74 in MeOH). Me glycoside, tetra-Ac Methyl 2-acetami-do-3,4,6-tri-0-acetyl-2-deoxy-a-D-gulo-pyranoside C,5H23N09 361.348... 

Me glycoside, 4-Ac Methyl 4-0-acetyl-2,3-anhydro-6-deoxy-a-D-gulopyranoside [6893-97-6]... 

Me glycoside, 4,6-O-benzylidene, 2-Ac Methyl 2-0-acetyl-4,6-0-benzylidene-3-bromo-3-deoxy-a-D-gulopyranoside C,6H,9Br06 387.226 Cryst. Mp 128-129°. [ag +67.5 (CHCI3). 

Me glycoside, 2,3-anhydro, 6-trityl Methyl 2,3-anhydro-4-bromo-4-deoxy-6-0-trityl-a-D-gulopyranoside [118360-83-1]... 

Me glycoside, 3-Ac Methyl 3-0-acetyl-6-deoxy-a-D-gulopyranoside CgHisOs 220.222... 

Me glycoside, tribenzoyl Methyl 2,4,6-tri-0-benzoyl-3-deoxy-3-iodo-f3-D-gulopyranoside [124314-31-4]... 

Me glycoside Methyl 6-deoxy-3-C-methyl-a-D-gulopyranoside CgHieO 192.211... 

Methyl 2-0-acetyl-3,4-anhydro-a-D-arabinopyranoside, A-504 Methyl 2-0-acetyl-3,4-anhydro-p-L-arabinopyranoside, A-504 Methyl 4-0-acetyl-2,3-anhydro-6-deoxy-a-D-gulopyranoside, A-527 Methyl 4-0-acetyl-2,3-anhydro-6-deoxy-p-D-gulopyranoside, A-527 Methyl 4-0-acetyl-2,3-anhydro-6-deoxy-a-D-mannopyranoside, A-687 Methyl 4-0-acetyl-3,6-anhydro-a-D-galactopyranoside, A-620 Methyl 5-0-acetyl-2,3-anhydro-a-D-lyxofuranoside, A-664 Methyl 5-0-acetyl-2,3-anhydro-p-D-lyxofuranoside, A-664 Methyl 3-0-acetyl-2,6-anhydro-4-0-methyl-p-D-mannopyranoside, A-678 Methyl 4-0-acetyl-2,3-anhydro-a-D-rhamnopyranoside, A-687 Methyl 5-0-acetyl-2,3-anhydro-a-D-ribofuranoside, A-690 Methyl 5-0-acetyl-2,3-anhydro-p-D-ribofuranoside, A-690 Methyl 4-0-acetyl-2,3-anhydro-p-D-ribopyranoside, A-693 Methyl 4-0-acetyl-2,3-anhydro-6-0-trityl-a-D-mannopyranoside, A-676 Methyl 2-0-acetyl-p-L-arabinopyranoside, M-153 Methyl 3-0 -acetyl-2-azido-4,6-0 -benzylidene-2-deoxy-a-D-mannopyranoside, A-912... 

Methyl 2-0-acetyl-4,6-0-benzylidene-3-bromo-3-deoxy-a-D-gulopyranoside, B-77... 

Methyl 6-ammo-2-acetamido-3,4-di-0-acetyl-p-i>idopyranoside, D-442 Methyl 2-Mnmo-3-ben2ylammo-2,3,6-trideoxy-a-L-gulopyranoside, D-476 Methyl 2-ammo-3-ben2ylamiiio-2,3,6-trideoxy-a-L-idopyraJioside, D-479 Methyl 2-amino-4,6-0-benzylidene-2-deoxy-a-i>altropyranoside, A-164 Methyl 2-amino-4,6-0-benzylidene-2-deoxy-p-i>altropyranoside, A-164 Methyl 5-amino-l,3-0-benzylidene-5-deoxy-p-i>fmctopyranoside, A-185 Methyl 3-amino-4,6-0-benzylidene-3-deoxy-a-i>glucopyranoside, A-267 Methyl 2-amino-4,6-0-benzylidene-2-deoxy-a-i>glucopyranoside, M-150 Methyl 2-amino-4,6-0-benzylidene-2-deoxy-p-i>glucopyranoside, M-150 Methyl 2-amino-4,6-0-benzylidene-2-deoxy-a-i>idopyranoside, A-291 Methyl 2-amino-4,6-(9-benzylidene-2-deoxy-p-i>idopyranoside, A-291 Methyl 3-amino-4,6-0-benzylidene-3-deoxy-a-i>idopyranoside, A-292 Methyl 5-amino-l,3-<5-benzylidene-5-deoxy-4-0-mesyl-(5-D-fructopyranoside, A-185... 

Methyl 2,3-anhydro-4-bromo-4-deoxy-a-L-lyxopyranoside, B-84 Methyl 2,3-anhydro-4-bromo-4-deoxy-6- O -trityl-a-D-gulopyranoside, B-78 Methyl 2,3-anhydro-4-chloro-4-deoxy-a-L-xylopyranoside, C-110 Methyl 2,3-anhydro-6-deoxy-a-D-allopyranoside, A-516 Methyl 2,3-anhydro-6-deoxy-a-L-allopyranoside, A-516 Methyl 3,6-anhydro-2-deoxy-4,5 7,8-di-0-isopropylidene-D-g-/ycer(3-D-ia/o-octonate, M-174... 

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