(1S,4R,5S,6S,1'R)-2-(1',2'-dihydroxyethyl)-5,6-(isopropylidenedioxy)-4-methoxy-3-phenylsulfonylcyclohex-2-enol

Base Information

Chemical Name:(1S,4R,5S,6S,1'R)-2-(1',2'-dihydroxyethyl)-5,6-(isopropylidenedioxy)-4-methoxy-3-phenylsulfonylcyclohex-2-enol
CAS No.:205743-87-9
Molecular Formula:C₁₈H₂₄O₈S
Molecular Weight:400.45
Hs Code.:

Synonyms:(1S,4R,5S,6S,1'R)-2-(1',2'-dihydroxyethyl)-5,6-(isopropylidenedioxy)-4-methoxy-3-phenylsulfonylcyclohex-2-enol

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Chemical Property of (1S,4R,5S,6S,1'R)-2-(1',2'-dihydroxyethyl)-5,6-(isopropylidenedioxy)-4-methoxy-3-phenylsulfonylcyclohex-2-enol

Chemical Property:

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Technology Process of (1S,4R,5S,6S,1'R)-2-(1',2'-dihydroxyethyl)-5,6-(isopropylidenedioxy)-4-methoxy-3-phenylsulfonylcyclohex-2-enol

There total 6 articles about (1S,4R,5S,6S,1'R)-2-(1',2'-dihydroxyethyl)-5,6-(isopropylidenedioxy)-4-methoxy-3-phenylsulfonylcyclohex-2-enol 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: 70.0%

: 205743-80-2
(1S,4R,5S,6S)-5,6-(isopropylidenedioxy)-4-methoxy-3-phenylsulfonyl-2-vinyl-cyclohex-2-enol

: 205743-87-9
(1S,4R,5S,6S,1'R)-2-(1',2'-dihydroxyethyl)-5,6-(isopropylidenedioxy)-4-methoxy-3-phenylsulfonylcyclohex-2-enol

: (1R,2S/2R,5S,6S,1'S)-2-(1',2'-dihydroxyethyl)-5,6-(isopropylidenedioxy)-4-methoxy-3-phenylsulfonylcyclohex-3-en-1,2-diol

Guidance literature:: With osmium(VIII) oxide; trimethylamine-N-oxide; In acetone; tert-butyl alcohol;
DOI:10.1016/S0957-4166(99)00358-4

Reference yield:

: 214278-38-3
5,6-exo-(isopropylidenedioxy)-2-phenylsulfonyl-7-oxabicyclo[2.2.1]hept-2-ene

: 205743-87-9
(1S,4R,5S,6S,1'R)-2-(1',2'-dihydroxyethyl)-5,6-(isopropylidenedioxy)-4-methoxy-3-phenylsulfonylcyclohex-2-enol

Guidance literature:: Multi-step reaction with 3 steps

1.1: n-BuLi / tetrahydrofuran / 0.5 h / 0 °C

1.2: 63 percent / toluene; tetrahydrofuran / 0.08 h / 0 °C

2.1: 71 percent / NaOMe / 0.33 h / 0 °C

3.1: 70 percent / aq. OsO₄; Me₃NO / 2-methyl-propan-2-ol; acetone

With osmium(VIII) oxide; n-butyllithium; trimethylamine-N-oxide; sodium methylate; In tetrahydrofuran; acetone; tert-butyl alcohol; 1.1: Metallation / 1.2: Ring cleavage / 2.1: olefination; methoxylation; desilylation / 3.1: Oxidation;
DOI:10.1016/S0957-4166(99)00358-4

Reference yield:

: 205743-78-8
(1S,2R,5R,6S)-5,6-(isopropylidenedioxy)-2-(trimethylsilylethynyl)-3-phenyl-sulfonylcyclohex-3-enol

: 205743-87-9
(1S,4R,5S,6S,1'R)-2-(1',2'-dihydroxyethyl)-5,6-(isopropylidenedioxy)-4-methoxy-3-phenylsulfonylcyclohex-2-enol

Guidance literature:: Multi-step reaction with 2 steps

1: 71 percent / NaOMe / 0.33 h / 0 °C

2: 70 percent / aq. OsO₄; Me₃NO / 2-methyl-propan-2-ol; acetone

With osmium(VIII) oxide; trimethylamine-N-oxide; sodium methylate; In acetone; tert-butyl alcohol; 1: olefination; methoxylation; desilylation / 2: Oxidation;
DOI:10.1016/S0957-4166(99)00358-4