(2S,3R,6S,7R)-2,7-bis(benzyloxymethyl)-2,3,6,7-dihydrooxepin-3,6-diol

Base Information

Chemical Name:(2S*,3R*,6S*,7R*)-2,7-bis(benzyloxymethyl)-2,3,6,7-dihydrooxepin-3,6-diol
CAS No.:244055-83-2
Molecular Formula:C₂₂H₂₆O₅
Molecular Weight:370.445
Hs Code.:

Synonyms:(2S*,3R*,6S*,7R*)-2,7-bis(benzyloxymethyl)-2,3,6,7-dihydrooxepin-3,6-diol

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Chemical Property of (2S*,3R*,6S*,7R*)-2,7-bis(benzyloxymethyl)-2,3,6,7-dihydrooxepin-3,6-diol

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Technology Process of (2S*,3R*,6S*,7R*)-2,7-bis(benzyloxymethyl)-2,3,6,7-dihydrooxepin-3,6-diol

There total 4 articles about (2S*,3R*,6S*,7R*)-2,7-bis(benzyloxymethyl)-2,3,6,7-dihydrooxepin-3,6-diol 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: 51.0%

: 100-39-0
benzyl bromide

: (2R,3S,6R,7S)-2,7-Bis-hydroxymethyl-2,3,6,7-tetrahydro-oxepine-3,6-diol

: 244055-83-2
(2S*,3R*,6S*,7R*)-2,7-bis(benzyloxymethyl)-2,3,6,7-dihydrooxepin-3,6-diol

Guidance literature:: (2R,3S,6R,7S)-2,7-Bis-hydroxymethyl-2,3,6,7-tetrahydro-oxepine-3,6-diol; With di(n-butyl)tin oxide; In toluene; for 5h; Heating;

benzyl bromide; With cesium fluoride; In N,N-dimethyl-formamide; at 20 ℃; for 17h;
DOI:10.1016/S0040-4020(99)00370-1

Reference yield:

: 244055-64-9
(2S*,7R*)-2,7-bis(triisopropylsilyloxymethyl)-2,7-dihydrooxepin-3,6-dione

: 244055-83-2
(2S*,3R*,6S*,7R*)-2,7-bis(benzyloxymethyl)-2,3,6,7-dihydrooxepin-3,6-diol

Guidance literature:: Multi-step reaction with 3 steps

1.1: 48 percent / Et₃SiH; TiCl₄ / CH₂Cl₂ / -78 °C

2.1: 59 percent / CF₂CO₂H / tetrahydrofuran / 30 h / 20 °C

3.1: Bu₂SnO / toluene / 5 h / Heating

3.2: 51 percent / CsF / dimethylformamide / 17 h / 20 °C

With triethylsilane; titanium tetrachloride; di(n-butyl)tin oxide; In tetrahydrofuran; dichloromethane; toluene; 1.1: Reduction / 2.1: Hydrolysis / 3.1: Dehydration / 3.2: Alkylation;
DOI:10.1016/S0040-4020(99)00370-1

Reference yield:

: 244055-65-0
(2S*,3R*,6S*,7R*)-2,7-bis(triisopropylsilyloxymethyl)-2,3,6,7-tetrahydrooxepin-3,6-diol

: 244055-83-2
(2S*,3R*,6S*,7R*)-2,7-bis(benzyloxymethyl)-2,3,6,7-dihydrooxepin-3,6-diol

Guidance literature:: Multi-step reaction with 2 steps

1.1: 59 percent / CF₂CO₂H / tetrahydrofuran / 30 h / 20 °C

2.1: Bu₂SnO / toluene / 5 h / Heating

2.2: 51 percent / CsF / dimethylformamide / 17 h / 20 °C

With di(n-butyl)tin oxide; In tetrahydrofuran; toluene; 1.1: Hydrolysis / 2.1: Dehydration / 2.2: Alkylation;
DOI:10.1016/S0040-4020(99)00370-1