methyl 4,5,7-tri-O-benzyl-2-deoxy-D-gluco-hept-2-ulosonate diethyldithioacetal

Base Information

• Chemical Name: methyl 4,5,7-tri-O-benzyl-2-deoxy-D-gluco-hept-2-ulosonate diethyldithioacetal
• CAS No.: 404377-25-9
• Molecular Formula: C₃₃H₄₂O₇S₂
• Molecular Weight: 614.824

Synonyms:methyl 4,5,7-tri-O-benzyl-2-deoxy-D-gluco-hept-2-ulosonate diethyldithioacetal

Chemical Property of methyl 4,5,7-tri-O-benzyl-2-deoxy-D-gluco-hept-2-ulosonate diethyldithioacetal

Chemical Property:

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Technology Process of methyl 4,5,7-tri-O-benzyl-2-deoxy-D-gluco-hept-2-ulosonate diethyldithioacetal

There total 1 articles about methyl 4,5,7-tri-O-benzyl-2-deoxy-D-gluco-hept-2-ulosonate diethyldithioacetal 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: 79.0%

glyoxylic acid methyl ester diethyl mercaptal (38564-39-5) + 2,3,5-tri-O-benzyl-D-arabinofuranose (160549-10-0) → methyl 4,5,7-tri-O-benzyl-2-deoxy-D-gluco-hept-2-ulosonate diethyldithioacetal (404377-25-9)

Guidance literature:

glyoxylic acid methyl ester diethyl mercaptal; With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at -20 ℃; for 2h;

2,3,5-tri-O-benzyl-D-arabinofuranose; With magnesium bromide; In tetrahydrofuran; hexane; at 0 - 20 ℃; for 3h;

DOI:10.1002/1099-0690(20021)2002:1<57::AID-EJOC57<3.0.CO;2-H

Reference yield: 76.0%

methyl 4,5,7-tri-O-benzyl-2-deoxy-D-gluco-hept-2-ulosonate diethyldithioacetal (404377-25-9) → methyl 4,5,7-tri-O-benzyl-2-deoxy-2-ethylthio-α-D-gluco-hept-2-ulopyranosonate (667917-77-3)

Guidance literature:

With N-iodo-succinimide; In acetonitrile; at -30 ℃; for 0.5h;

DOI:10.1021/jo0353029

Reference yield: 73.0%

methyl 4,5,7-tri-O-benzyl-2-deoxy-D-gluco-hept-2-ulosonate diethyldithioacetal (404377-25-9) → methyl 4,5,7-tri-O-benzyl-α-D-gluco-hept-2-ulopyranosonate (136305-59-4)

Guidance literature:

With N-iodo-succinimide; In acetone; at 20 ℃; for 0.5h;

DOI:10.1002/1099-0690(20021)2002:1<57::AID-EJOC57<3.0.CO;2-H

upstream raw materials:

glyoxylic acid methyl ester diethyl mercaptal

2,3,5-tri-O-benzyl-D-arabinofuranose

Downstream raw materials:

methyl 4,5,7-tri-O-benzyl-α-D-gluco-hept-2-ulopyranosonate

methyl 4,5,7-tri-O-benzyl-2-deoxy-2-ethylthio-α-D-gluco-hept-2-ulopyranosonate

methyl 3-azido-4,5,7-tri-O-benzyl-2,3-dideoxy-2-ethylthio-α-D-manno-hept-2-ulopyranosonate

methyl 3-O-acetyl-4,5,7-tri-O-benzyl-α-D-gluco-hept-2-ulopyranosonate

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