(1R,2S,3R,4S,5R,6R)-3,4-(isopropylidenedioxy)-5,6-epoxycyclohexane-1,2-diol

Base Information

Chemical Name:(1R,2S,3R,4S,5R,6R)-3,4-(isopropylidenedioxy)-5,6-epoxycyclohexane-1,2-diol
CAS No.:145107-28-4
Molecular Formula:C₉H₁₄O₅
Molecular Weight:202.207
Hs Code.:

Synonyms:(1R,2S,3R,4S,5R,6R)-3,4-(isopropylidenedioxy)-5,6-epoxycyclohexane-1,2-diol

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Chemical Property of (1R,2S,3R,4S,5R,6R)-3,4-(isopropylidenedioxy)-5,6-epoxycyclohexane-1,2-diol

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Technology Process of (1R,2S,3R,4S,5R,6R)-3,4-(isopropylidenedioxy)-5,6-epoxycyclohexane-1,2-diol

There total 3 articles about (1R,2S,3R,4S,5R,6R)-3,4-(isopropylidenedioxy)-5,6-epoxycyclohexane-1,2-diol 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: 60.0%

: 130669-74-8
(1S,2S,5R,6R)-3-bromo-5,6-epoxy-1,2-O-isopropylidencyclohex-3-en-1,2-diol

: 130669-72-6,137501-12-3
(3aS,4R,5S,7aS)-7-bromo-3a,4,5,7a-tetrahydro-2,2-dimethyl-1,3-benzodioxole-4,5-diol

: 145107-28-4
(1R,2S,3R,4S,5R,6R)-3,4-(isopropylidenedioxy)-5,6-epoxycyclohexane-1,2-diol

Guidance literature:: (1S,2S,5R,6R)-3-bromo-5,6-epoxy-1,2-O-isopropylidencyclohex-3-en-1,2-diol; With sodium periodate; ruthenium(III) chloride dihydrate; In water; acetonitrile; at 0 ℃; for 0.0833333h;

With sodium tetrahydroborate; In water; acetonitrile; at 0 - 20 ℃; for 0.333333h;
DOI:10.1002/ejoc.201801424

Reference yield:

: 108-86-1,52753-63-6
bromobenzene

: 130669-72-6,137501-12-3
(3aS,4R,5S,7aS)-7-bromo-3a,4,5,7a-tetrahydro-2,2-dimethyl-1,3-benzodioxole-4,5-diol

: 145107-28-4
(1R,2S,3R,4S,5R,6R)-3,4-(isopropylidenedioxy)-5,6-epoxycyclohexane-1,2-diol

Guidance literature:: Multi-step reaction with 3 steps

1.1: dioxygenase in E_. coli (JM₁₀₉ (pDTG₆₀₁)) / toluene / Microbiological reaction

2.1: toluene-4-sulfonic acid; Dess-Martin periodane / 0.5 h / 20 °C

2.2: 16 h / 0 - 20 °C

3.1: sodium periodate; ruthenium(III) chloride dihydrate / water; acetonitrile / 0.08 h / 0 °C

3.2: 0.33 h / 0 - 20 °C

With sodium periodate; ruthenium(III) chloride dihydrate; Dess-Martin periodane; toluene-4-sulfonic acid; In water; toluene; acetonitrile;
DOI:10.1002/ejoc.201801424

Reference yield:

: 67451-62-1,82683-92-9,132958-32-8,130792-45-9
cis-(1S,2S)-1,2-dihydroxy-3-bromocyclohexa-3,5-diene

: 130669-72-6,137501-12-3
(3aS,4R,5S,7aS)-7-bromo-3a,4,5,7a-tetrahydro-2,2-dimethyl-1,3-benzodioxole-4,5-diol

: 145107-28-4
(1R,2S,3R,4S,5R,6R)-3,4-(isopropylidenedioxy)-5,6-epoxycyclohexane-1,2-diol

Guidance literature:: Multi-step reaction with 2 steps

1.1: toluene-4-sulfonic acid; Dess-Martin periodane / 0.5 h / 20 °C

1.2: 16 h / 0 - 20 °C

2.1: sodium periodate; ruthenium(III) chloride dihydrate / water; acetonitrile / 0.08 h / 0 °C

2.2: 0.33 h / 0 - 20 °C

With sodium periodate; ruthenium(III) chloride dihydrate; Dess-Martin periodane; toluene-4-sulfonic acid; In water; acetonitrile;
DOI:10.1002/ejoc.201801424