(3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyl-5-1-[(tetrahydro-2H-2-pyranyloxy)methyl]vinylperhydrofuro[2,3-d][1,3]dioxole

Base Information

Chemical Name:(3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyl-5-1-[(tetrahydro-2H-2-pyranyloxy)methyl]vinylperhydrofuro[2,3-d][1,3]dioxole
CAS No.:1414099-40-3
Molecular Formula:C₂₂H₃₀O₆
Molecular Weight:390.477
Hs Code.:

Synonyms:(3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyl-5-1-[(tetrahydro-2H-2-pyranyloxy)methyl]vinylperhydrofuro[2,3-d][1,3]dioxole

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Chemical Property of (3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyl-5-1-[(tetrahydro-2H-2-pyranyloxy)methyl]vinylperhydrofuro[2,3-d][1,3]dioxole

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Technology Process of (3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyl-5-1-[(tetrahydro-2H-2-pyranyloxy)methyl]vinylperhydrofuro[2,3-d][1,3]dioxole

There total 4 articles about (3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyl-5-1-[(tetrahydro-2H-2-pyranyloxy)methyl]vinylperhydrofuro[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: 56.0%

: 1414099-34-5
C₂₁H₂₈O₇

: 2065-66-9
methyl-triphenylphosphonium iodide

: 1414099-40-3
(3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyl-5-1-[(tetrahydro-2H-2-pyranyloxy)methyl]vinylperhydrofuro[2,3-d][1,3]dioxole

Guidance literature:: methyl-triphenylphosphonium iodide; With potassium tert-butylate; In tetrahydrofuran; at -10 ℃; for 5h;

C₂₁H₂₈O₇; In tetrahydrofuran; at 20 ℃; for 12h;
DOI:10.1039/c2ob26615f

Reference yield:

: 22529-61-9
(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol

: 1414099-40-3
(3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyl-5-1-[(tetrahydro-2H-2-pyranyloxy)methyl]vinylperhydrofuro[2,3-d][1,3]dioxole

Guidance literature:: Multi-step reaction with 3 steps

1.1: toluene-4-sulfonic acid / dichloromethane / 3 h / 0 - 20 °C

2.1: oxalyl dichloride / dichloromethane; dimethyl sulfoxide / 3 h / -78 °C

2.2: 0.5 h / -78 °C

3.1: potassium tert-butylate / tetrahydrofuran / 5 h / -10 °C

3.2: 12 h / 20 °C

With oxalyl dichloride; potassium tert-butylate; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide;
DOI:10.1039/c2ob26615f

Reference yield:

: 912652-02-9
(1R)-1-[(3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethylperhydrofuro[2,3-d][1,3]dioxol-5-yl]-2-(tetrahydro-2H-2-pyranyloxy)ethan-1-ol

: 1414099-40-3
(3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyl-5-1-[(tetrahydro-2H-2-pyranyloxy)methyl]vinylperhydrofuro[2,3-d][1,3]dioxole

Guidance literature:: Multi-step reaction with 2 steps

1.1: oxalyl dichloride / dichloromethane; dimethyl sulfoxide / 3 h / -78 °C

1.2: 0.5 h / -78 °C

2.1: potassium tert-butylate / tetrahydrofuran / 5 h / -10 °C

2.2: 12 h / 20 °C

With oxalyl dichloride; potassium tert-butylate; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide;
DOI:10.1039/c2ob26615f