ethyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: ethyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside
• CAS No.: 151992-75-5
• Molecular Formula: C₂₂H₂₅N₃O₄S
• Molecular Weight: 427.524

Synonyms:ethyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside

Chemical Property of ethyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside

Chemical Property:

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Technology Process of ethyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside

There total 7 articles about ethyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside 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: 97.0%

ethyl 2-amino-3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside → ethyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside (151992-75-5)

Guidance literature:

With dmap; triflic azide; In dichloromethane; for 16h;

DOI:10.1016/S0040-4020(01)01241-8

Reference yield:

2-((6S,7R,8aS)-8-benzyloxy-6-ethylsulfanyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-isoindole-1,3-dione (129519-27-3) → ethyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside (151992-75-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / ethylenediamine / butan-1-ol / 14 h / 90 °C

2: 97 percent / triflyl azide; DMAP / CH₂Cl₂ / 16 h

With dmap; triflic azide; ethylenediamine; In dichloromethane; butan-1-ol;

DOI:10.1016/S0040-4020(01)01241-8

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → ethyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside (151992-75-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / p-toluenesulfonic acid / dimethylformamide / 4 h

2: 3.65 g / NaH / dimethylformamide / 0.17 h

With sodium hydride; toluene-4-sulfonic acid; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(97)10238-1

upstream raw materials:

ethyl iodide

1-S-acetyl-2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside

2-((6S,7R,8aS)-8-benzyloxy-6-ethylsulfanyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-isoindole-1,3-dione

benzaldehyde dimethyl acetal

Downstream raw materials:

6-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol 1-phosphate

Phosphoric acid (1R,2R,3S,4R,5R,6R)-2-((2R,3R,4R,5S,6R)-3-azido-4-benzyloxy-6-benzyloxymethyl-5-hydroxy-tetrahydro-pyran-2-yloxy)-3,4,5,6-tetrahydroxy-cyclohexyl ester dibenzyl ester

Methyl O-(methyl 2,3,4-tri-O-acetyl-α-L-idopyranosyluronate)-(1->4)-O-(2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-O-(tert-butyl 2,3-di-O-benzyl-β-D-glucopyranosid)uronate

ethyl 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-(methyl 2,3,4-tri-O-acetyl-α-L-idopyranosyluronate)-1-thio-β-D-glucopyranoside

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