(2S,3S,4S)-3-benzyloxy-4-benzyloxymethyl-2-(p-toluenesulfonyl)oxymethyl-4-hydroxytetrahydrofuran

Base Information

Chemical Name:(2S,3S,4S)-3-benzyloxy-4-benzyloxymethyl-2-(p-toluenesulfonyl)oxymethyl-4-hydroxytetrahydrofuran
CAS No.:223591-06-8
Molecular Formula:C₂₇H₃₀O₇S
Molecular Weight:498.597
Hs Code.:

Synonyms:(2S,3S,4S)-3-benzyloxy-4-benzyloxymethyl-2-(p-toluenesulfonyl)oxymethyl-4-hydroxytetrahydrofuran

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Chemical Property of (2S,3S,4S)-3-benzyloxy-4-benzyloxymethyl-2-(p-toluenesulfonyl)oxymethyl-4-hydroxytetrahydrofuran

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Technology Process of (2S,3S,4S)-3-benzyloxy-4-benzyloxymethyl-2-(p-toluenesulfonyl)oxymethyl-4-hydroxytetrahydrofuran

There total 6 articles about (2S,3S,4S)-3-benzyloxy-4-benzyloxymethyl-2-(p-toluenesulfonyl)oxymethyl-4-hydroxytetrahydrofuran 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: 82.8%

: 98-59-9
p-toluenesulfonyl chloride

: 223590-99-6
(2S,3S,4S)-3-benzyloxy-4-benzyloxymethyl-2-hydroxymethyl-4-hydroxytetrahydrofuran

: 223591-06-8
(2S,3S,4S)-3-benzyloxy-4-benzyloxymethyl-2-(p-toluenesulfonyl)oxymethyl-4-hydroxytetrahydrofuran

Guidance literature:: With dmap; In dichloromethane; at 20 ℃; for 10h;
DOI:10.1021/jo000275x

Reference yield:

: 223591-10-4
(2R,3S,4S)-3-benzyloxy-4-benzyloxymethyl-2-formyl-4-hydroxytetrahydrofuran

: 223591-06-8
(2S,3S,4S)-3-benzyloxy-4-benzyloxymethyl-2-(p-toluenesulfonyl)oxymethyl-4-hydroxytetrahydrofuran

Guidance literature:: Multi-step reaction with 2 steps

1: 5.776 g / NaBH₄ / methanol / 0.33 h / 20 °C

2: 82.8 percent / DMAP / CH₂Cl₂ / 10 h / 20 °C

With dmap; sodium tetrahydroborate; In methanol; dichloromethane; 1: Reduction / 2: Tosylation;
DOI:10.1021/jo000275x

Reference yield:

: 223590-98-5
(1S,3RS,4R,7S)-7-benzyloxy-1-benzyloxymethyl-3-methoxy-2,5-dioxabicyclo[2.2.1]heptane

: 223591-06-8
(2S,3S,4S)-3-benzyloxy-4-benzyloxymethyl-2-(p-toluenesulfonyl)oxymethyl-4-hydroxytetrahydrofuran

Guidance literature:: Multi-step reaction with 3 steps

1: aq. AcOH / 3.5 h / 50 °C

2: 5.776 g / NaBH₄ / methanol / 0.33 h / 20 °C

3: 82.8 percent / DMAP / CH₂Cl₂ / 10 h / 20 °C

With dmap; sodium tetrahydroborate; acetic acid; In methanol; dichloromethane; 1: Hydrolysis / 2: Reduction / 3: Tosylation;
DOI:10.1021/jo000275x