(-)-(3aR,6S,6aR)-6-benzyloxymethyl-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole

Base Information

Chemical Name:(-)-(3aR,6S,6aR)-6-benzyloxymethyl-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole
CAS No.:681811-41-6
Molecular Formula:C₁₅H₂₀O₄
Molecular Weight:264.321
Hs Code.:

Synonyms:(-)-(3aR,6S,6aR)-6-benzyloxymethyl-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole

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Chemical Property of (-)-(3aR,6S,6aR)-6-benzyloxymethyl-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole

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Technology Process of (-)-(3aR,6S,6aR)-6-benzyloxymethyl-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole

There total 12 articles about (-)-(3aR,6S,6aR)-6-benzyloxymethyl-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole 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%

: 1610459-65-8
1,2-O-isopropylidene-3-deoxy-α-D-apio-D-furanose

: 100-39-0
benzyl bromide

: 681811-41-6
(-)-(3aR,6S,6aR)-6-benzyloxymethyl-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole

Guidance literature:: 1,2-O-isopropylidene-3-deoxy-α-D-apio-D-furanose; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 ℃; for 0.166667h; Inert atmosphere;

benzyl bromide; In N,N-dimethyl-formamide; mineral oil; at 0 - 25 ℃; for 18h; Inert atmosphere;
DOI:10.1021/jo500659e

Reference yield:

: dithiocarbonic acid O-(6-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl) ester S-methyl ester

: 681811-41-6
(-)-(3aR,6S,6aR)-6-benzyloxymethyl-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole

Guidance literature:: With triethyl borane; tri-n-butyl-tin hydride; In hexane; benzene; at 20 ℃; for 3h;
DOI:10.1016/j.bmc.2003.12.002

Reference yield:

: 14048-35-2
(-)-(3aR,6S,6aR)-6-hydroxymethyl-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol

: 681811-41-6
(-)-(3aR,6S,6aR)-6-benzyloxymethyl-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole

Guidance literature:: Multi-step reaction with 3 steps

1.1: nBu₂SnO / toluene / 2 h / 140 - 150 °C

1.2: 73 percent / nBu₄NBr / toluene / 90 - 100 °C

2.1: NaH / tetrahydrofuran / 1 h / 20 °C

2.2: tetrahydrofuran / 1 h / 20 °C

3.1: 1.82 g / Et₃B; nBu₃SnH / benzene; hexane / 3 h / 20 °C

With triethyl borane; tri-n-butyl-tin hydride; sodium hydride; di(n-butyl)tin oxide; In tetrahydrofuran; hexane; toluene; benzene;
DOI:10.1016/j.bmc.2003.12.002