((3aR,5R,7R,7aS)-5,7-dihydroxy-2,2-dimethylhexahydro-1,3-benzodioxol-5-yl)methyl 4-methylbenzenesulfonate

Base Information

Chemical Name:((3aR,5R,7R,7aS)-5,7-dihydroxy-2,2-dimethylhexahydro-1,3-benzodioxol-5-yl)methyl 4-methylbenzenesulfonate
CAS No.:166757-80-8
Molecular Formula:C₁₇H₂₄O₇S
Molecular Weight:372.439
Hs Code.:

Synonyms:((3aR,5R,7R,7aS)-5,7-dihydroxy-2,2-dimethylhexahydro-1,3-benzodioxol-5-yl)methyl 4-methylbenzenesulfonate

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Chemical Property of ((3aR,5R,7R,7aS)-5,7-dihydroxy-2,2-dimethylhexahydro-1,3-benzodioxol-5-yl)methyl 4-methylbenzenesulfonate

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Technology Process of ((3aR,5R,7R,7aS)-5,7-dihydroxy-2,2-dimethylhexahydro-1,3-benzodioxol-5-yl)methyl 4-methylbenzenesulfonate

There total 4 articles about ((3aR,5R,7R,7aS)-5,7-dihydroxy-2,2-dimethylhexahydro-1,3-benzodioxol-5-yl)methyl 4-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: 90.0%

: 101917-46-8
(3aS,4R,6R,7aR)-6-Hydroxymethyl-2,2-dimethyl-hexahydro-benzo[1,3]dioxole-4,6-diol

: 98-59-9
p-toluenesulfonyl chloride

: 166757-80-8
((3aR,5R,7R,7aS)-5,7-dihydroxy-2,2-dimethylhexahydro-1,3-benzodioxol-5-yl)methyl 4-methylbenzenesulfonate

Guidance literature:: (3aS,4R,6R,7aR)-6-Hydroxymethyl-2,2-dimethyl-hexahydro-benzo[1,3]dioxole-4,6-diol; With di(n-butyl)tin oxide; In benzene; at 100 ℃; for 6h;

p-toluenesulfonyl chloride; In benzene; at 0 ℃; for 0.5h;
DOI:10.1016/S0040-4020(01)00195-8

Reference yield: 16.0%

: 101917-46-8
(3aS,4R,6R,7aR)-6-Hydroxymethyl-2,2-dimethyl-hexahydro-benzo[1,3]dioxole-4,6-diol

: 98-59-9
p-toluenesulfonyl chloride

: 166757-80-8
((3aR,5R,7R,7aS)-5,7-dihydroxy-2,2-dimethylhexahydro-1,3-benzodioxol-5-yl)methyl 4-methylbenzenesulfonate

: Toluene-4-sulfonic acid (3aR,5R,7R,7aS)-7-hydroxy-5-hydroxymethyl-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-5-yl ester

: C₂₄H₃₀O₉S₂

Guidance literature:: With pyridine; dmap; In dichloromethane; at 0 - 20 ℃;
DOI:10.1021/ja00137a026

Reference yield:

: 32384-42-2
(1S,3R,4S,5R)-3,4-O-isopropylidene-1,5-quinic lactone

: 166757-80-8
((3aR,5R,7R,7aS)-5,7-dihydroxy-2,2-dimethylhexahydro-1,3-benzodioxol-5-yl)methyl 4-methylbenzenesulfonate

Guidance literature:: Multi-step reaction with 2 steps

1.1: sodium tetrahydroborate; ethanol / 2.5 h / -5 - 0 °C

2.1: sodium sulfate; di(n-butyl)tin oxide / toluene / 6 h / Molecular sieve; Reflux

2.2: 0 - 20 °C

With sodium tetrahydroborate; ethanol; di(n-butyl)tin oxide; sodium sulfate; In toluene;
DOI:10.1002/adsc.202101080