(1R,2R,3S)-1-O-(Phenoxythionocarbonyl)-2,3-O-isopropylidene-5-(methoxycarbonyl)-4-cyclohexene-1,2,3-triol

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Chemical Name:(1R,2R,3S)-1-O-(Phenoxythionocarbonyl)-2,3-O-isopropylidene-5-(methoxycarbonyl)-4-cyclohexene-1,2,3-triol
CAS No.:154929-04-1
Molecular Formula:C₁₈H₂₀O₆S
Molecular Weight:364.419
Hs Code.:

Synonyms:(1R,2R,3S)-1-O-(Phenoxythionocarbonyl)-2,3-O-isopropylidene-5-(methoxycarbonyl)-4-cyclohexene-1,2,3-triol

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Chemical Property of (1R,2R,3S)-1-O-(Phenoxythionocarbonyl)-2,3-O-isopropylidene-5-(methoxycarbonyl)-4-cyclohexene-1,2,3-triol

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Technology Process of (1R,2R,3S)-1-O-(Phenoxythionocarbonyl)-2,3-O-isopropylidene-5-(methoxycarbonyl)-4-cyclohexene-1,2,3-triol

There total 1 articles about (1R,2R,3S)-1-O-(Phenoxythionocarbonyl)-2,3-O-isopropylidene-5-(methoxycarbonyl)-4-cyclohexene-1,2,3-triol 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: 67.0%

: 109430-30-0
(3aS,7R,7aR)-methyl 7-hydroxy-2,2-dimethyl-3a,6,7,7a-tetrahydrobenzo[d][1,3]dioxole-5-carboxylate

: 1005-56-7
phenylcarbonochloridothioate

: 154929-04-1
(1R,2R,3S)-1-O-(Phenoxythionocarbonyl)-2,3-O-isopropylidene-5-(methoxycarbonyl)-4-cyclohexene-1,2,3-triol

Guidance literature:: With pyridine; dmap; In dichloromethane; at 23 ℃; for 2h;
DOI:10.1021/jo00088a065

Reference yield:

: 154929-04-1
(1R,2R,3S)-1-O-(Phenoxythionocarbonyl)-2,3-O-isopropylidene-5-(methoxycarbonyl)-4-cyclohexene-1,2,3-triol

: 115225-55-3
6a-Carba-β-D-fructopyranose

Guidance literature:: Multi-step reaction with 5 steps

1: 76 percent / Bu₃SnH, (t-BuO)2 / toluene / 1.5 h / Heating

2: 81 percent / OsO₄, trimethylamine oxide dihydrate, H₂O, pyridine / 2-methyl-propan-2-ol / 2 h / Heating

3: camphorsulfonic acid / CH₂Cl₂ / 2.5 h

4: 75 percent / DIBAL-H / tetrahydrofuran

5: 91 percent / aq. trifluoroacetic acid / 3.5 h / 23 °C

With pyridine; osmium(VIII) oxide; trimethylamine-N-oxide; di-tert-butyl peroxide; camphor-10-sulfonic acid; water; tri-n-butyl-tin hydride; diisobutylaluminium hydride; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; toluene; tert-butyl alcohol;
DOI:10.1021/jo00088a065