Ribopyranoside methyl 3,4-dichloro-3,4-dideoxy

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... 

Me glycoside Methyl 3,4-dichloro S,4-dideoxy-p-D-ribopyranoside C6H10CI2O3 201.049 Syrup. [a]o -55 (c, 0.8 in MeOH). 

Methyl 3,4-di-0-acetyl-2-deoxy-2-iodo-p-D-ribopyranoside, D-270 Methyl 3,5-di-0-benzoyl-2-bromo-2-deoxy-a-D-ribofuranoside, B-92 Methyl 2,3-di-0-benzoyl-5-bromo-5-deoxy-p-D-ribofuranoside, B-93 Methyl 2,4-di-0-benzoyl-3-deoxy-3-iodo-p-L-ribopyranoside, D-271 Methyl 3,5-di-0-benzoyl-2-0-methyl-p-D-ribofuranoside, M-208 Methyl 3,5-di-O-benzoyl-p-D-ribofuranoside, M-208 Methyl 3,5-di-O-benzyl-a-D-ribofuranoside, M-208 Methyl 3,4-dichloro-3,4-dideoxy-p-D-ribopyranoside, D-545 Methyl 2-C-formyl-3,4-0-isopropylidene-p-D-ribopyranoside, F-23 Methyl 3,4-0-isopropylidene-2-0-methyl-p-D-ribopyranoside, M-209 Methyl 2,3-0-isopropylidene-5-5 -methyl-5-thio-p-D-ribofuranoside, T-91 Methyl 2,3-0-isopropylidene-p-D-ribofuranoside, 1-74 Methyl 2,3-0-isopropylidene-p-L-ribofuranoside, 1-74 Methyl 2,3-0-isopropylidene-p-D-ribopyranoside, M-209 Methyl 3,4-0-isopropylidene-p-D-ribopyranoside, M-209 Methyl 2,3-0-isopropylidene-5-thio-p-D-ribofuranoside, T-91 Methyl 2,3-0-isopropylidene-5-thio-p-D-ribopyranoside, T-91 Methyl 3,4-0-isopropylidene-5-thio-p-D-ribopyranoside, T-91... 

Metltyl 2,4-di-0-ben2 yl-3-bromo-3 deoxy-(3-D-arabinopyranoside, B-63 Methyl 2,4-di-0-benzoyl-3-bromo-3-deoxy-a-D-lyxopyranoside, B-83 Methyl 2,5-di-0-ben2 yl-3-bromo-3-deoxy-a-D-xylofuranoside, B-103 Methyl 2,5-di-0-ben2 yl-3-bromo-3-deoxy-(3-D-xylofuranoside, B-103 Methyl 2,4-di-0-benzoyl-3-deoxy-3-iodo-p-L-ribopyranoside, D-271 Methyl 3,6-dibromo-3, dideoxy-(3-D-allopyranoside, 9CI, D-523 Methyl 3,6-dibromo-3,6-dideoxy-(3-D-glua>pyranoside, 9CI, D-532 Methyl 3,4--glycero -pent-2-enopyranoside,... 

Methyl 4,6-dichloro-4,6-dideoxy-a-i>galactopyraiioside, 9CI, 8CI, D-542 Methyl 4,6-dichloro-4,6-dideoxy-p-i> lactopyranoside, D-542 Methyl 4,6-dichloro-4,6-dideoxy-a-D-glucopyranoside, D-543 Methyl 3,4-dichloro-3,4-dideoxy-p-D-ribopyranoside, D-545 Methyl 3,4-dichloro-2,3,4-trideoxy-p-i>gfpcero -pent-2-enopyranoside,... 

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