Methyl 6-chloro-6-deoxy

Many other glycosides have been subjected to selective chlorination with sulfuryl chloride. Methyl /3-L-arabinopyranoside afforded methyl 4-chloro-4-deoxy-a-D-xylopyranoside 2,3-di(chlorosulfate) in 29% yield, whereas the a-L anomer gave357 methyl 3,4-dichloro-3,4-dideoxy-/3-i)-ribopyranoside 2-(chlorosulfate) (30%). Methyl /3-d-ribopyranoside was converted into methyl 3,4-dichloro-3,4-dideoxy-a-L-arabinopyranoside through the action of pyridine hydrochloride on its 2,3,4-tri(chlorosulfate).358 Methyl a-D-lyxopyranoside gave only the 2,3,4-tri(chlorosulfate),353 as would be expected from the disposition of its hydroxyl groups, similar to that in the rhamno- and manno-pyranosides. Methyl a-D-altropyranoside was transformed into the 6-chloro-6-deoxy 2,3,4-tri(chlorosulfate) derivative in 80% yield.353... 

S. S. Thomas, J. Plenkiewicz, E. R. Ison, M. Bols, W. Zou, W. A. Szarek, and R. Kisilevsky, Influence of monosaccharide derivatives on liver cell glycosaminoglycan synthesis 3-deoxy-D-xylo-hexose (3-deoxy-o-gaIactose) and methyl (methyl 4-chloro-4-deoxy- 3-D-galacto-pyranosid)uronate, Biochim. Biophys. Acta 1272 37 (1995). 

Of incidental interest is the observation that an w-chlorine atom may be replaced by iodine under Oldham and Rutherford s conditions, without affecting secondary sulfonyloxy groups. Thus, Levene and Tipson107 found that 5-chloro-5-deoxy-2,3-di-0-tosyl-uridine affords the corresponding 5-deoxy-5-iodo derivative plus sodium chloride on the other hand, methyl 4-chloro-4-deoxy-2,3,6-tri-0-tosyl-a-D- glucoside gives117 the 4-chloro-4,6-dideoxy-6-iodo derivative. These observations, taken... 

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. ... 

The slow periodate oxidation of methyl 4-chloro-4-deoxy-a-D-gluco-pyranoside (and of the bromo analog ) has been noted. Periodate oxidation of methyl a-n-glucopyranoside is extremely slow, because of the... 

Me glycoside Methyl 4-chloro-4-deoxy-fl-D-arabinopyranoside C6H11CIO4 182.603 Needles (EtOAc). Mp 152°. [a]o +237 (c, 0.96 in MeOH). 

Me glycoside, 2-mesyl Methyl 4-chloro-4-deoxy-2-0-mesyl-a-L-xylopyranoside [18417-51-1]... 

Methyl 2-0-benzoyl-a-D-arabinofiiraiioside, M-152 Methyl 2-0-benzoyl-3-0-benzyl-a-i>ajabmofiiraiioside, M-152 Methyl 2-0-benzoyl-3,4-0-benzylidene-p-L-ajabinopyraiioside, M-153 Methyl 5-0-benzoyl-3-bromo-3-deoxy-p-i>arabmofiiranoside, B-63 Methyl 5-0-benzoyl-3-deoxy-3-iodo-a-i>ajabmofiiranoside, D-250 Methyl 4-0-benzoyl-2-deoxy-2-iodo-p-L-arabinopyranoside, D-249 Methyl 2-0-benzoyl-3,4-0-ethylidene-p-L-arabinopyranoside, M-153 Methyl 2-0-benzoyl-3,4-0-isopropylidene-p-L-ajabinopyraiioside, M-197 Methyl 2-O-benzyl-p-D-arabmofuranoside, M-152 Methyl 2-0-benzyl-p-L-arabinopyranoside, M-153 Methyl 3,4-O-benzylidene-p-L-arabinopyranoside, M-153 Methyl 3,4-0-benzylidene-2-0-tosyl-p-L-arabinopyranoside, M-153 Methyl 2-0-benzyl-3,4-0-isopropylidene-p-L-ajabinopyranoside, M-197 Methyl 2-bromo-2-deoxy- -D-arabinopyranoside, B-62 Methyl 3-bromo-3-deoxy-P-D-arabinopyranoside, B-63 Methyl 2-chloro-2-deoxy-a-D-arabinofuranoside, C-74 Methyl 2-chloro-2-deoxy-P-D-arabinofuranoside, C-74 Methyl 4-chloro-4-deoxy-P-D-arabinopyranoside, C-75 Methyl 3,5-di-0-acetyl-2-bromo-2-deoxy-a-D-arabinofuranoside, B-62 Methyl 3,5-di-0-acetyl-2-bromo-2-deoxy-P-D-arabinofuranoside, B-62 Methyl 3,5-di-0-acetyl-2-chloro-2-deoxy-a-D-arabinofuranoside, C-74 Methyl 3,5-di-0-acetyl-2-chloro-2-deoxy-P-D-arabinofuranoside, C-74 Methyl 3.4-di-0-acetyl-2-chloro-2-deoxy-a-D-arabinopyranoside, C-74 Methyl 3,4-di-0-acetyl-2-deoxy-2-iodo-a-D-arabinopyranoside, D-249 Methyl 3,4-di-0-acetyl-2-deoxy-2-iodo-a-L-arabinopyranoside, D-249 Methyl 3,5-di-0-acetyl-2-0-methyl-a-D-arabinofuranoside, M-152 Methyl 3,5-di-0-acetyl-2-0-methyl-p-D-arabinofuranoside, M-152 Methyl 3,4-di-0-acetyl-2-0-methyl-p-L-arabinopyranoside, M-153 Methyl 2,3-di-0-acetyl-4-0-methyl-a-DL-arabinopyranoside, M-153 Methyl 2,3-di-O-benzoyl-p-L-arabinopyranoside, M-153 Methyl 3,5-di-0-benzoyl-2-bromo-2-deoxy-p-D-arabinofuranoside, B-62 Methyl 2,4-di-0-benzoyl-3-bromo-3-deoxy-p-D-arabinopyranoside, B-63 Methyl 2,3-di-0-benzoyl-5-0-tosyl-a-L-arabinofuranoside, M-152 Methyl 2,3-di-O-benzyl-a-L-arabinofuranoside, M-152 Methyl 2,3-di-O-benzyl-P-L-arabinofuranoside, M-152 Methyl 3,5-di-0-benzyl-2-chloro-2-deoxy-a-D-arabinofuranoside, C-74 Methyl 3,4-di-0-benzyl-2-deoxy-2-C-(tosylcarbamoyl)-a-L-arabinopyranoside, C-8... 

Methyl 4-0-benz yl-3-deoxy-3-iodo-p-L-xylopyranoside, D-280 Methyl 2-0-benz yl-3,5-0-isopropylidene-a-D-xylofuranoside, M-216 Methyl 5-0-benz yl-3-0-methyl-a-i>xylofuranoside, M-216 Methyl 5-0-benz yl-2-0-methyl-p-i>xylofuranoside, M-216 Methyl 3-0-benz yl-a-D-xylopyranoside, M-217 Methyl 5-0-benzyl-2-deoxy-2-fluoro-p-i>xylofuranoside, D-118 Methyl 5-0-benzyl-2,3-di-0-methyl-a-i>xylofuranoside, M-216 Methyl 2-0-benzyl-3,5-0-isopropylidene-a-D-xylofuranoside, M-216 Methyl 2-0-benzyl-3,5-0-isopropylidene-p-D-xylofuranoside, M-216 Methyl 5-0-benzyl-3-0-methyl-a-D-xylofuranoside, M-216 Methyl 2-0-benzyl-a-i>xylofuranoside, M-216 Methyl 3-bromo-3-deoxy-p-D-xylopyraiioside, B-103 Methyl 4-chloro-4-deoxy-2-0-mesyl-a-L-xylopyranoside, C-110 Methyl 3-chloro-3-deoxy-5-0-trityl-p-D-xylofuranoside, C-109 Methyl 3-chloro-3-deoxy-5-0-trityl-p-D-xylopyranoside, C-109 Methyl 2-chloro-2-deoxy-p-D-xylopyranoside, C-108 Methyl 3-chloro-3-deoxy-p-D-xylopyranoside, C-109 Methyl 2-deoxy-2-fluoro-p-D-xylofuranoside, D-118... 

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