4-pentenyl 4-O-benzyl-3-O-(4-bromobenzyl)-6-O-triisopropylsilyl-β-D-mannopyranoside

Base Information

Chemical Name:4-pentenyl 4-O-benzyl-3-O-(4-bromobenzyl)-6-O-triisopropylsilyl-β-D-mannopyranoside
CAS No.:429679-64-1
Molecular Formula:C₃₄H₅₁BrO₆Si
Molecular Weight:663.765
Hs Code.:

Synonyms:4-pentenyl 4-O-benzyl-3-O-(4-bromobenzyl)-6-O-triisopropylsilyl-β-D-mannopyranoside

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Chemical Property of 4-pentenyl 4-O-benzyl-3-O-(4-bromobenzyl)-6-O-triisopropylsilyl-β-D-mannopyranoside

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Technology Process of 4-pentenyl 4-O-benzyl-3-O-(4-bromobenzyl)-6-O-triisopropylsilyl-β-D-mannopyranoside

There total 5 articles about 4-pentenyl 4-O-benzyl-3-O-(4-bromobenzyl)-6-O-triisopropylsilyl-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:

: (2R,4S,5R,6R)-5-Benzyloxy-4-(4-bromo-benzyloxy)-2-pent-4-enyloxy-6-triisopropylsilanyloxymethyl-dihydro-pyran-3-one

: 429679-64-1
4-pentenyl 4-O-benzyl-3-O-(4-bromobenzyl)-6-O-triisopropylsilyl-β-D-mannopyranoside

Guidance literature:: With sodium tetrahydroborate; In methanol; dichloromethane; at 20 ℃; for 16h;
DOI:10.1002/1099-0690(200203)2002:5<826::AID-EJOC826>3.0.CO;2-2

Reference yield:

: 100-39-0
benzyl bromide

: 429679-64-1
4-pentenyl 4-O-benzyl-3-O-(4-bromobenzyl)-6-O-triisopropylsilyl-β-D-mannopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1.1: 93 percent / sodium hydride / dimethylformamide / 2 h / 20 °C

2.1: dimethyldioxirane / CH₂Cl₂; acetone / 0.25 h / 0 °C

2.2: 87 percent / ZnCl₂ / diethyl ether; CH₂Cl₂ / 16 h / 20 °C

3.1: DMSO; Ac₂O / toluene / 48 h / 20 °C

4.1: NaBH₄ / CH₂Cl₂; methanol / 16 h / 20 °C

With sodium tetrahydroborate; 3,3-dimethyldioxirane; acetic anhydride; sodium hydride; dimethyl sulfoxide; In methanol; dichloromethane; N,N-dimethyl-formamide; acetone; toluene;
DOI:10.1002/1099-0690(200203)2002:5<826::AID-EJOC826>3.0.CO;2-2

Reference yield:

: 294637-61-9
1,5-anhydro-3-O-(4-bromobenzyl)-2-deoxy-6-O-triisopropylsilyl-D-arabino-hex-1-enitol

: 429679-64-1
4-pentenyl 4-O-benzyl-3-O-(4-bromobenzyl)-6-O-triisopropylsilyl-β-D-mannopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1.1: 93 percent / sodium hydride / dimethylformamide / 2 h / 20 °C

2.1: dimethyldioxirane / CH₂Cl₂; acetone / 0.25 h / 0 °C

2.2: 87 percent / ZnCl₂ / diethyl ether; CH₂Cl₂ / 16 h / 20 °C

3.1: DMSO; Ac₂O / toluene / 48 h / 20 °C

4.1: NaBH₄ / CH₂Cl₂; methanol / 16 h / 20 °C

With sodium tetrahydroborate; 3,3-dimethyldioxirane; acetic anhydride; sodium hydride; dimethyl sulfoxide; In methanol; dichloromethane; N,N-dimethyl-formamide; acetone; toluene;
DOI:10.1002/1099-0690(200203)2002:5<826::AID-EJOC826>3.0.CO;2-2