2-(benzyloxycarbonylamino)-2-deoxy-3,4:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal

Base Information

• Chemical Name: 2-(benzyloxycarbonylamino)-2-deoxy-3,4:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal
• CAS No.: 73707-67-2
• Molecular Formula: C₂₂H₃₃NO₈
• Molecular Weight: 439.506

Synonyms:2-(benzyloxycarbonylamino)-2-deoxy-3,4:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal

Chemical Property of 2-(benzyloxycarbonylamino)-2-deoxy-3,4:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal

Chemical Property:

Purity/Quality:

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Technology Process of 2-(benzyloxycarbonylamino)-2-deoxy-3,4:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal

There total 5 articles about 2-(benzyloxycarbonylamino)-2-deoxy-3,4:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 75.0%

methanol (67-56-1) + [(R)-2,2-Bis-propylsulfanyl-1-((4S,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-ethyl]-carbamic acid benzyl ester (241156-32-1) → [(R)-2,2-Dimethoxy-1-((4S,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-ethyl]-carbamic acid benzyl ester (73707-67-2)

Guidance literature:

With bis-[(trifluoroacetoxy)iodo]benzene; for 0.25h; Ambient temperature;

DOI:10.1016/S0968-0896(98)00264-8

Reference yield: 68.6%

2-carbobenzyloxyamino-2-deoxy-D-glucopyranose (3006-58-4,13030-01-8,42890-10-8,42973-23-9,77059-32-6,121785-09-9,7474-40-0) + 2,2-dimethoxy-propane (77-76-9) → 2-(benzyloxycarbonylamino)-2-deoxy-3,4:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal (73707-67-2)

Guidance literature:

With toluene-4-sulfonic acid; In 1,4-dioxane; at 60 - 65 ℃; for 2h;

DOI:10.1016/S0008-6215(00)83838-0

Reference yield:

2-carbobenzyloxyamino-2-deoxy-D-glucopyranose (3006-58-4,13030-01-8,42890-10-8,42973-23-9,77059-32-6,121785-09-9,7474-40-0) + 2,2-dimethoxy-propane (77-76-9) → [(R)-2,2-Dimethoxy-1-((4S,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-ethyl]-carbamic acid benzyl ester (73707-67-2)

Guidance literature:

toluene-4-sulfonic acid; In 1,4-dioxane; at 60 - 70 ℃; for 2h;

DOI:10.1016/0008-6215(84)85110-1

upstream raw materials:

2-carbobenzyloxyamino-2-deoxy-D-glucopyranose

2,2-dimethoxy-propane

methanol

[(R)-2,2-Bis-propylsulfanyl-1-((4S,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-ethyl]-carbamic acid benzyl ester

Downstream raw materials:

(3S,4S)-4-Acetyl-1-[(R)-2,2-dimethoxy-1-((4S,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-ethyl]-3-ethyl-azetidin-2-one

1<(1',2'-dideoxy-3',4';5',6'-di-O-isopropylidene-1',1'-dimethoxy)-D-2'-glucosyl>-3β-ethyl-4β-(trans-α-methylstyryl)-2-azetidinone

2-(benzyloxycarbonylamino)-2-deoxy-3,4-O-isopropylidene-aldehydo-D-glucose dimethyl acetal

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