(1S,2R,3S,4S,5S)-3,4-O-sulfinyl-1-[(phenylmethoxy)methyl]-2-(phenylmethoxy)bicyclo[3.1.0]hexane-3,4-diol

Base Information

Chemical Name:(1S,2R,3S,4S,5S)-3,4-O-sulfinyl-1-[(phenylmethoxy)methyl]-2-(phenylmethoxy)bicyclo[3.1.0]hexane-3,4-diol
CAS No.:828935-17-7
Molecular Formula:C₂₁H₂₂O₅S
Molecular Weight:386.469
Hs Code.:

Synonyms:(1S,2R,3S,4S,5S)-3,4-O-sulfinyl-1-[(phenylmethoxy)methyl]-2-(phenylmethoxy)bicyclo[3.1.0]hexane-3,4-diol

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (1S,2R,3S,4S,5S)-3,4-O-sulfinyl-1-[(phenylmethoxy)methyl]-2-(phenylmethoxy)bicyclo[3.1.0]hexane-3,4-diol

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Technology Process of (1S,2R,3S,4S,5S)-3,4-O-sulfinyl-1-[(phenylmethoxy)methyl]-2-(phenylmethoxy)bicyclo[3.1.0]hexane-3,4-diol

There total 7 articles about (1S,2R,3S,4S,5S)-3,4-O-sulfinyl-1-[(phenylmethoxy)methyl]-2-(phenylmethoxy)bicyclo[3.1.0]hexane-3,4-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: 99.0%

: 828935-16-6
(1S,2R,3S,4S,5S)-1-[(phenylmethoxy)methyl]-2-(phenylmethoxy)bicyclo[3.1.0]hexane-3,4-diol

: 828935-17-7
(1S,2R,3S,4S,5S)-3,4-O-sulfinyl-1-[(phenylmethoxy)methyl]-2-(phenylmethoxy)bicyclo[3.1.0]hexane-3,4-diol

Guidance literature:: With thionyl chloride;
DOI:10.1081/NCN-120021954

Reference yield:

: 495397-65-4
ethyl (1S,3S,4S,5S)-3,4-isopropylenedioxy-2-oxobicyclo[3.1.0]hexane-1-carboxylate

: 828935-17-7
(1S,2R,3S,4S,5S)-3,4-O-sulfinyl-1-[(phenylmethoxy)methyl]-2-(phenylmethoxy)bicyclo[3.1.0]hexane-3,4-diol

Guidance literature:: Multi-step reaction with 4 steps

1: 55 percent / DIBAL-H / toluene; tetrahydrofuran / 1 h / -78 °C

2: 62 percent / NaH / dimethylformamide / 3 h / 75 °C

3: 91 percent / Dowex 50WX₈-100 / methanol / 72 h / 20 °C

4: 89 percent / SOCl₂; Et₃N / CH₂Cl₂ / 0.17 h / 0 °C

With thionyl chloride; Dowex 50WX₈-100; sodium hydride; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo0487606

Reference yield:

: 828935-14-4,389626-30-6
(1S,2R,3S,4S,5S)-3,4-O-isopropylidene-1-(hydroxymethyl)bicyclo[3.1.0]hexan-2-ol

: 828935-17-7
(1S,2R,3S,4S,5S)-3,4-O-sulfinyl-1-[(phenylmethoxy)methyl]-2-(phenylmethoxy)bicyclo[3.1.0]hexane-3,4-diol

Guidance literature:: Multi-step reaction with 3 steps

1: 62 percent / NaH / dimethylformamide / 3 h / 75 °C

2: 91 percent / Dowex 50WX₈-100 / methanol / 72 h / 20 °C

3: 89 percent / SOCl₂; Et₃N / CH₂Cl₂ / 0.17 h / 0 °C

With thionyl chloride; Dowex 50WX₈-100; sodium hydride; triethylamine; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo0487606