ethyl 4-O-allyl-2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside S-oxide

Base Information

Chemical Name:ethyl 4-O-allyl-2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside S-oxide
CAS No.:439684-01-2
Molecular Formula:C₂₅H₃₁N₃O₅S
Molecular Weight:485.604
Hs Code.:

Synonyms:ethyl 4-O-allyl-2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside S-oxide

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Chemical Property of ethyl 4-O-allyl-2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside S-oxide

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Technology Process of ethyl 4-O-allyl-2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside S-oxide

There total 5 articles about ethyl 4-O-allyl-2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside S-oxide 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%

: 200938-30-3
ethyl 4-O-allyl-2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside

: 439684-01-2
ethyl 4-O-allyl-2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside S-oxide

Guidance literature:: With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -78 - -20 ℃; for 0.5h;
DOI:10.1016/S0040-4020(01)01241-8

Reference yield:

: 129519-27-3
2-((6S,7R,8aS)-8-benzyloxy-6-ethylsulfanyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-isoindole-1,3-dione

: 439684-01-2
ethyl 4-O-allyl-2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside S-oxide

Guidance literature:: Multi-step reaction with 5 steps

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

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

3: 85 percent / NaBH₃CN / tetrahydrofuran

4: 100 percent / NaH / dimethylformamide

5: 97 percent / m-CPBA / CH₂Cl₂ / 0.5 h / -78 - -20 °C

With dmap; triflic azide; sodium hydride; sodium cyanoborohydride; ethylenediamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; butan-1-ol;
DOI:10.1016/S0040-4020(01)01241-8

Reference yield:

: 151992-76-6
Ethyl 2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside

: 439684-01-2
ethyl 4-O-allyl-2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside S-oxide

Guidance literature:: Multi-step reaction with 2 steps

1: 100 percent / NaH / dimethylformamide

2: 97 percent / m-CPBA / CH₂Cl₂ / 0.5 h / -78 - -20 °C

With sodium hydride; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)01241-8