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

Base Information

Chemical Name:(2S,3S,4S)-4-acetoxy-3-benzyloxy-4-benzyloxymethyl-2-((p-toluenesulfonyl)oxymethyl)tetrahydrofuran
CAS No.:296250-69-6
Molecular Formula:C₂₉H₃₂O₈S
Molecular Weight:540.634
Hs Code.:

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

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

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

There total 6 articles about (2S,3S,4S)-4-acetoxy-3-benzyloxy-4-benzyloxymethyl-2-((p-toluenesulfonyl)oxymethyl)tetrahydrofuran 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: 84.2%

: 108-24-7
acetic anhydride

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

: 296250-69-6
(2S,3S,4S)-4-acetoxy-3-benzyloxy-4-benzyloxymethyl-2-((p-toluenesulfonyl)oxymethyl)tetrahydrofuran

Guidance literature:: With dmap; In pyridine; at 20 ℃; for 2h;
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

: 296250-69-6
(2S,3S,4S)-4-acetoxy-3-benzyloxy-4-benzyloxymethyl-2-((p-toluenesulfonyl)oxymethyl)tetrahydrofuran

Guidance literature:: Multi-step reaction with 7 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

6: 82.8 percent / DMAP / CH₂Cl₂ / 10 h / 20 °C

7: 84.2 percent / DMAP / pyridine / 2 h / 20 °C

With pyridine; hydrogenchloride; dmap; sodium tetrahydroborate; sodium hydride; acetic acid; In pyridine; methanol; dichloromethane; N,N-dimethyl-formamide; 1: sulfonation / 2: Hydrolysis / 3: Cyclization / 4: Hydrolysis / 5: Reduction / 6: Tosylation / 7: Acetylation;
DOI:10.1021/jo000275x

Reference yield:

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

: 296250-69-6
(2S,3S,4S)-4-acetoxy-3-benzyloxy-4-benzyloxymethyl-2-((p-toluenesulfonyl)oxymethyl)tetrahydrofuran

Guidance literature:: Multi-step reaction with 3 steps

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

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

3: 84.2 percent / DMAP / pyridine / 2 h / 20 °C

With dmap; sodium tetrahydroborate; In pyridine; methanol; dichloromethane; 1: Reduction / 2: Tosylation / 3: Acetylation;
DOI:10.1021/jo000275x