(3aR,5R,6R,6aR)-6-(benzyloxy)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-6-vinyltetrahydrofuro-[2,3-d][1,3]dioxole

Base Information

Chemical Name:(3aR,5R,6R,6aR)-6-(benzyloxy)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-6-vinyltetrahydrofuro-[2,3-d][1,3]dioxole
CAS No.:96212-44-1
Molecular Formula:C₂₁H₂₈O₆
Molecular Weight:376.45
Hs Code.:

Synonyms:(3aR,5R,6R,6aR)-6-(benzyloxy)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-6-vinyltetrahydrofuro-[2,3-d][1,3]dioxole

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Chemical Property of (3aR,5R,6R,6aR)-6-(benzyloxy)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-6-vinyltetrahydrofuro-[2,3-d][1,3]dioxole

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Technology Process of (3aR,5R,6R,6aR)-6-(benzyloxy)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-6-vinyltetrahydrofuro-[2,3-d][1,3]dioxole

There total 8 articles about (3aR,5R,6R,6aR)-6-(benzyloxy)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-6-vinyltetrahydrofuro-[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: 97.0%

: 100-39-0
benzyl bromide

: 51996-47-5
(3aR,5R,6R,6aR)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-6-vinyltetrahydrofuro[2,3-d][1,3]-dioxol-6-ol

: 96212-44-1
(3aR,5R,6R,6aR)-6-(benzyloxy)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-6-vinyltetrahydrofuro-[2,3-d][1,3]dioxole

Guidance literature:: (3aR,5R,6R,6aR)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-6-vinyltetrahydrofuro[2,3-d][1,3]-dioxol-6-ol; With sodium hydride; In N,N-dimethyl-formamide; at 50 ℃; for 1h;

benzyl bromide; In N,N-dimethyl-formamide; at 20 ℃; for 16h; Further stages.;
DOI:10.1039/b101364p

Reference yield: 76.0%

: 39838-77-2,51996-47-5
(3aR,5R,6aR)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-6-vinyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol

: 100-39-0
benzyl bromide

: 96212-44-1
(3aR,5R,6R,6aR)-6-(benzyloxy)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-6-vinyltetrahydrofuro-[2,3-d][1,3]dioxole

Guidance literature:: With tetrabutylammomium bromide; sodium hydride;
DOI:10.1021/jo00209a050

Reference yield:

: 582-52-5
1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

: 96212-44-1
(3aR,5R,6R,6aR)-6-(benzyloxy)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-6-vinyltetrahydrofuro-[2,3-d][1,3]dioxole

Guidance literature:: Multi-step reaction with 3 steps

1.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / 3 h / 85 - 90 °C

2.1: tetrahydrofuran / 0.5 h / 0 - 20 °C

3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 15 - 60 °C

3.2: 5 h / 15 - 20 °C

With sodium hydride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; N,N-dimethyl-formamide; mineral oil;