6- Deoxy-6- -£>-glucopyranose

Deoxy-2- [(methylnitrosamino)carbonyl]amino -D-glucopyranose, 2-deoxy-2-(3-... 

U067. . U076. . Ethane, 1,2-dibromo-Ethane, 1,1-dichloro U206. . D-Glucopyranose, 2-deoxy-2(3-methyl-3-nitrosoureido)-... 

StreptDzotocin D-Glucopyranose, 2-deoxy-2-[[(methylnitrosoamino)carbonyl]amino]- 18883-66-4... 

Conversion of l,6-anhydro-4-0-benzyl-2 deoxy 2-fluoro-p-D-glucopyranose to the corresponding oxo derivative is earned out by ruthenium tetroxide generated in situ from ruthenium dioxide [54] (equation 49)... 

Chemical Name 2-Deoxy-2-(3-methyl-3-nitrosoureido)-D-glucopyranose Common Name -... 

Amino-3-0-[(fl)-1-carboxyethyl]-2-deoxy-p-D-glucopyranose (p-muramic acid)... 

Deoxy-2-phenyl-a-D-glucopyranose or 2-deoxy-2-C-phenyl-a-D-glucopyranose or (2fl)-2-deoxy-2-phenyl-a-D-arab/no-hexopyranose... 

Deoxy-2-dimethoxyphosphoryl-D-glucopyranose (this usage of phosphoryl is given in [13], Section D, Rule 5.68, and [14], p. 65) or dimethyl 2-deoxy-D-glucopyranos-2-ylphosphonate... 

Amino-5-deoxy-D-glucopyranose trivial name nojirimycin... 

Note 1. The alternative name using a substituent prefix (see 2-Carb-35.1) is 2-amino-1-0,2-N-(benzylylidene)-2-deoxy-a-D-glucopyranose. 

Nigerose Nojirimycin Noviose a-D-Glucopyranosyl-(1- 3)-D-glucose 5- Amino-5-deoxy-D-glucopyranose 6- Deoxy-5-C-methyl-4-Omethyl-L-/yxo-hexose... 

CN 2-[[3-(acetyIamino)-5-(acetylmethylamino) 2,4,6-triiodobenzoyl]amino]-2-deoxy-D-glucopyranose... 

Compound 278 was convertible into 2-amino-2-deoxy- (280) and 2,7-diamino-2,7-dideoxy-a-DL-carba-glucopyranose (281) derivatives in satisfactory yields. 

Sharpless reaction of the enantiomeric alkenes (47) produced the precursors for 2-amino-2-deoxy-o -D and -L-carba-glucopyranoses. These compounds were converted into the penta-7V,0-acetates by the following sequence. Replacement of the bromo group with an acetate ion, treatment with sodium in liquid ammonia, and peracetylation. 

An alternative synthesis,by method h, was conducted by coupling 357 and 1,6-anhydro-4-0-(3,4-anhydro-6-deoxy-a-D-galactopyranosyl)-a-D-glucopyranose (392a) in 2-propanol at 120° this yielded a diastereoiso-meric mixture, from which, after the usual treatment, amylostatin (XG) was isolated in 20% yield. 

Chitin, a y3-(1 4)-linked polysaccharide consisting mainly of 2-ace-tamido-2-deoxy-D-glucopyranose units, is soluble in liquid HF, and is grad-... 

Trideoxy-2,3,4-trifluoro-D-galacto- and -gluco-pyranosyl derivatives 391 and 392 have been prepared from l,6-anhydro-4-(9-benzyl-2-deoxy-2-fluoro-/ -D-glucopyranose (385) by use of DAST, through several intermediates, as shown [385 386,10% 387- 388,72% 389 390,90% refl. toluene (for 385) or dichloromethane (for 387 and 389), 24 h]. 

Deoxy-2-[ F]fluoro-3-(9-methyl-D-glucopyranose was prepared by the reaction of methyl 4,6-0-benzylidene-3-0-methyl-2-0-triflyl-) -D-manno-pyranoside (159) with CsH F2, and the possibility of its use as an imaging agent was examined." ... 

Several 1 -phosphates of deoxyfluoro sugars were prepared, and their acid-catalyzed hydrolysis was studied. 2-Deoxy-2-fluoro- (580), 3-deoxy-3-fluoro- (582), 4-deoxy-4-fluoro- (583), and 6-deoxy-6-fluoro-a-D-gluco-pyranosyl phosphates (584) were prepared by treatment of the corresponding per-( -acetylated )9-D-glucopyranoses with phosphoric acid [the p anomer (581) of 580 was prepared by a different method]. The first and second ionization constants (pA a, and pA a2) of these compounds were determined potentiometrically, as well as by the F-n.m.r. chemical shifts at a series of pH values, and then the rate constants of hydrolysis for neutral (B) and monoanion (C) were decided. The first-order rate-constants (k) for 580-584 and a-D-glucopyranosyl phosphate (in Af HCIO4,25 °) were 0.068, 0.175, 0.480, 0.270, 1.12, and 4.10 (all as x lOVs), respectively. The rate... 

As part of a study on cell-surface glycans, 4-0-(2-deoxy-2-fluoro-a-D-mannopyranosyl)-D-glucopyranose (612) was prepared. Condensation of 6-0-acetyl-1,2,3-tri-0-benzyl-)3-D-glucopyranose with the protected 2-deoxy-2-fluoro-tt-D-mannopyranosyl chloride 611 gave the corresponding A-0- a- and y -D-mannopyranosyl)-D-glucopyranoside derivatives (a/) =... 

Amide derivatives have proved especially useful sugars for study by c.d. spectroscopy. The amide substituent is the same as the chromophore found in proteins, so that its optical properties have been extensively studied both experimentally and theoretically. 2-Acetamido sugars are found in many glycoproteins. The structure of 2-acetamido-2-deoxy-a-D-glucopyranose is given as an example in formula 7. 

Acetamido-2-deoxy-D-galactopyranose (—), and 2-Acetamido-2-deoxy-D-mannopyranose ( ) at Anomeric Equilibrium in Aqueous Solution (redrawn from Ref. 28), and 2-Acetamido-2-deoxy-D-glucopyranose (- -) at Anomeric Equilibrium in Aqueous Solution. (Redrawn from Ref. 29.)... 

Fig. 18.—The Circular Dichroism of a 2-Acetamido-2-deoxy-D-glucopyranose Film. (Redrawn from Ref. 37.)...

In muramic acid, the 2-hydroxyl group of D-glucose is replaced by an amine group, and a lactic acid group is attached to OH-3. The structure of muramic acid [2-amino-3-0-(D-l-carboxyethyl)-2-deoxy-D-glucopyranose] is given in formula 12. 

Support for this result was obtained from the taste of 1,5-anhydrohexitols, which, only for purposes of comparison, can be regarded as 1-deoxyal-dopyranoses. 1,5-Anhydro-D-glucitol (that is, the incorrectly named 1-deoxy-D-glucopyranose ) (14), 1,5-anhydro-D-mannitol ( 1-deoxy-D-mannopyranose or 2-deoxy-D-fructopyranose ) (15), and 1,5-anhydro-D-galactitol ( l-deoxy-o-galactopyranose ) (16) are all purely sweet, without any trace of bitterness. Furthermore, the complete absence of bitterness of 1,5-anhydromannitol (16) clearly indicates that the anomeric... 

Ana,6s (2 AM6S (where I = a-L-iduronic acid, ANA6S = 2-acetamido-2-deoxy-a-D-glucopyranose 6-sulfate, G = / -D-glucuronic acid, and AMes = 2,5-anhydro-D-mannitol 6-sulfate, the last arising from 2-deoxy-... 

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