(3aR,5R,6S,6aR)-2,2-dimethyl-5-(prop-1-en-2-yl)tetrahydrofuro-[2,3-d][1,3]dioxol-6-yl4-methylbenzenesulfonate

Base Information

Chemical Name:(3aR,5R,6S,6aR)-2,2-dimethyl-5-(prop-1-en-2-yl)tetrahydrofuro-[2,3-d][1,3]dioxol-6-yl4-methylbenzenesulfonate
CAS No.:78785-04-3
Molecular Formula:C₁₇H₂₂O₆S
Molecular Weight:354.424
Hs Code.:

Synonyms:(3aR,5R,6S,6aR)-2,2-dimethyl-5-(prop-1-en-2-yl)tetrahydrofuro-[2,3-d][1,3]dioxol-6-yl4-methylbenzenesulfonate

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Chemical Property of (3aR,5R,6S,6aR)-2,2-dimethyl-5-(prop-1-en-2-yl)tetrahydrofuro-[2,3-d][1,3]dioxol-6-yl4-methylbenzenesulfonate

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Technology Process of (3aR,5R,6S,6aR)-2,2-dimethyl-5-(prop-1-en-2-yl)tetrahydrofuro-[2,3-d][1,3]dioxol-6-yl4-methylbenzenesulfonate

There total 4 articles about (3aR,5R,6S,6aR)-2,2-dimethyl-5-(prop-1-en-2-yl)tetrahydrofuro-[2,3-d][1,3]dioxol-6-yl4-methylbenzenesulfonate 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: 85.0%

: 1779-49-3
Methyltriphenylphosphonium bromide

: 78785-03-2
(3aR,5S,6R,6aR)-5-acetyl-2,2-dimethyltetrahydrofuro[2,3-d]-[1,3]dioxol-6-yl 4-methylbenzenesulfonate

: 78785-04-3
(3aR,5R,6S,6aR)-2,2-dimethyl-5-(prop-1-en-2-yl)tetrahydrofuro-[2,3-d][1,3]dioxol-6-yl4-methylbenzenesulfonate

Guidance literature:: With n-butyllithium; In tetrahydrofuran; at -10 - 0 ℃;
DOI:10.1002/cber.19811140605

Reference yield: 78.0%

: 78785-03-2
(3aR,5S,6R,6aR)-5-acetyl-2,2-dimethyltetrahydrofuro[2,3-d]-[1,3]dioxol-6-yl 4-methylbenzenesulfonate

: 78785-04-3
(3aR,5R,6S,6aR)-2,2-dimethyl-5-(prop-1-en-2-yl)tetrahydrofuro-[2,3-d][1,3]dioxol-6-yl4-methylbenzenesulfonate

Guidance literature:: With n-butyllithium; Methyltriphenylphosphonium bromide; In tetrahydrofuran; hexane; at 20 ℃; for 1h;
DOI:10.1039/c5ob00481k

Reference yield:

: 78785-02-1
6-Desoxy-1,2-O-isopropyliden-3-O-(4-methylphenylsulfonyl)-α-D-glucofuranose

: 78785-04-3
(3aR,5R,6S,6aR)-2,2-dimethyl-5-(prop-1-en-2-yl)tetrahydrofuro-[2,3-d][1,3]dioxol-6-yl4-methylbenzenesulfonate

Guidance literature:: Multi-step reaction with 2 steps

1: 85 percent / pyridinium chlorochromate, NaOAc

2: 85 percent / BuLi / tetrahydrofuran / -10 - 0 °C

With n-butyllithium; sodium acetate; pyridinium chlorochromate; In tetrahydrofuran;
DOI:10.1002/cber.19811140605