thioethyl 2-O-pivaloyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside-(1->6)-3,4-di-O-benzyl-2-O-pivaloyl-β-D-mannopyranoside

Base Information

Chemical Name:thioethyl 2-O-pivaloyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside-(1->6)-3,4-di-O-benzyl-2-O-pivaloyl-β-D-mannopyranoside
CAS No.:226919-73-9
Molecular Formula:C₅₉H₇₂O₁₂S
Molecular Weight:1005.28
Hs Code.:

Synonyms:thioethyl 2-O-pivaloyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside-(1->6)-3,4-di-O-benzyl-2-O-pivaloyl-β-D-mannopyranoside

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Chemical Property of thioethyl 2-O-pivaloyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside-(1->6)-3,4-di-O-benzyl-2-O-pivaloyl-β-D-mannopyranoside

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Technology Process of thioethyl 2-O-pivaloyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside-(1->6)-3,4-di-O-benzyl-2-O-pivaloyl-β-D-mannopyranoside

There total 12 articles about thioethyl 2-O-pivaloyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside-(1->6)-3,4-di-O-benzyl-2-O-pivaloyl-β-D-mannopyranoside 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: 83.0%

: 226919-63-7
dibutyl 2-O-pivaloyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside phosphate

: 226919-70-6
ethyl 3,4-di-O-benzyl-2-O-pivaloyl-1-thio-β-D-mannopyranoside

: 226919-73-9
thioethyl 2-O-pivaloyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside-(1->6)-3,4-di-O-benzyl-2-O-pivaloyl-β-D-mannopyranoside

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -78 ℃; for 0.166667h;
DOI:10.1021/ol9905452

Reference yield:

: 1011723-04-8
glucal epoxide

: 226919-73-9
thioethyl 2-O-pivaloyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside-(1->6)-3,4-di-O-benzyl-2-O-pivaloyl-β-D-mannopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: CH₂Cl₂ / -78 °C

2: DMAP / tetrahydrofuran / 1 h / 20 °C

3: 83 percent / trimethylsilyl triflate / CH₂Cl₂ / 0.17 h / -78 °C

With dmap; trimethylsilyl trifluoromethanesulfonate; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ol9905452

Reference yield:

: ((3R,4R,5S)-4,5-Bis-benzyloxy-2,7-dioxa-bicyclo[4.1.0]hept-3-ylmethoxy)-triisopropyl-silane

: 226919-73-9
thioethyl 2-O-pivaloyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside-(1->6)-3,4-di-O-benzyl-2-O-pivaloyl-β-D-mannopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1.1: 66 percent / TFAA

2.1: Ac₂O / dimethylsulfoxide

2.2: 72 percent / NaBH₄

3.1: DMAP

4.1: 89 percent / acetic acid; tetrabutylammonium fluoride / tetrahydrofuran / 6 h

5.1: 82 percent / TMSOTf / CH₂Cl₂ / 0.5 h / -78 °C

With dmap; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; acetic anhydride; acetic acid; trifluoroacetic anhydride; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide;
DOI:10.1021/ja016227r