(2S,3S,4S)-3-benzyloxy-4-benzyloxymethyl-2-hydroxymethyl-4-hydroxytetrahydrofuran

Base Information

Chemical Name:(2S,3S,4S)-3-benzyloxy-4-benzyloxymethyl-2-hydroxymethyl-4-hydroxytetrahydrofuran
CAS No.:223590-99-6
Molecular Formula:C₂₀H₂₄O₅
Molecular Weight:344.408
Hs Code.:

Synonyms:(2S,3S,4S)-3-benzyloxy-4-benzyloxymethyl-2-hydroxymethyl-4-hydroxytetrahydrofuran

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Chemical Property of (2S,3S,4S)-3-benzyloxy-4-benzyloxymethyl-2-hydroxymethyl-4-hydroxytetrahydrofuran

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Technology Process of (2S,3S,4S)-3-benzyloxy-4-benzyloxymethyl-2-hydroxymethyl-4-hydroxytetrahydrofuran

There total 5 articles about (2S,3S,4S)-3-benzyloxy-4-benzyloxymethyl-2-hydroxymethyl-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: 95.0%

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

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

Guidance literature:: With sodium tetrahydroborate; In methanol; at 20 ℃;
DOI:10.1016/S0040-4039(00)01607-5

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 2 steps

1: aq. AcOH / 3.5 h / 50 °C

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

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

Reference yield:

: 153186-10-8
((3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol

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

Guidance literature:: Multi-step reaction with 5 steps

1: pyridine / 0.33 h / 20 °C

2: 11.896 g / aq. HCl / 10 h

3: NaH / dimethylformamide / 2 h / 20 °C

4: aq. AcOH / 3.5 h / 50 °C

5: 5.776 g / NaBH₄ / methanol / 0.33 h / 20 °C

With pyridine; hydrogenchloride; sodium tetrahydroborate; sodium hydride; acetic acid; In methanol; N,N-dimethyl-formamide; 1: sulfonation / 2: Hydrolysis / 3: Cyclization / 4: Hydrolysis / 5: Reduction;
DOI:10.1021/jo000275x