(S)-1-((1S,2R,3S,4R,5S)-2,3,4,5-Tetrakis-benzyloxy-cyclohexyl)-ethane-1,2-diol

Base Information

Chemical Name:(S)-1-((1S,2R,3S,4R,5S)-2,3,4,5-Tetrakis-benzyloxy-cyclohexyl)-ethane-1,2-diol
CAS No.:921771-19-9
Molecular Formula:C₃₆H₄₀O₆
Molecular Weight:568.71
Hs Code.:

Synonyms:(S)-1-((1S,2R,3S,4R,5S)-2,3,4,5-Tetrakis-benzyloxy-cyclohexyl)-ethane-1,2-diol

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Chemical Property of (S)-1-((1S,2R,3S,4R,5S)-2,3,4,5-Tetrakis-benzyloxy-cyclohexyl)-ethane-1,2-diol

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Technology Process of (S)-1-((1S,2R,3S,4R,5S)-2,3,4,5-Tetrakis-benzyloxy-cyclohexyl)-ethane-1,2-diol

There total 13 articles about (S)-1-((1S,2R,3S,4R,5S)-2,3,4,5-Tetrakis-benzyloxy-cyclohexyl)-ethane-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: 82.0%

: 921771-17-7
(2S)-2-[(1S,2R,3S,4R,5S)-2,3,4,5-tetrakis-benzyloxy-cyclohexyl]-1,4-dioxa-spiro[4.5]decane

: 921771-19-9
(S)-1-((1S,2R,3S,4R,5S)-2,3,4,5-Tetrakis-benzyloxy-cyclohexyl)-ethane-1,2-diol

Guidance literature:: With acetic acid; at 20 ℃; for 14h;
DOI:10.1021/jo061717t

Reference yield:

: (R)-(S)-5-(1,4-Dioxa-spiro[4.5]dec-2-yl)-cyclohex-3-enol

: 921771-19-9
(S)-1-((1S,2R,3S,4R,5S)-2,3,4,5-Tetrakis-benzyloxy-cyclohexyl)-ethane-1,2-diol

Guidance literature:: Multi-step reaction with 9 steps

1.1: 71 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / 3 h

2.1: 92 percent / LiAlH₄ / diethyl ether / 1 h / -60 °C

3.1: 92 percent / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 2 h / 20 °C

4.1: 89 percent / m-CPBA / 1,2-dichloro-ethane / 8 h / 20 °C

5.1: diphenyl diselenide; sodium borohydride / ethanol / 2 h / 20 °C

5.2: 41 percent / aq. H₂O₂ / ethanol; tetrahydrofuran / 1.5 h / 70 °C

6.1: NaH / tetrahydrofuran / 2 h / 20 °C

6.2: 69 percent / HMPA / tetrahydrofuran / 12 h / 20 °C

7.1: 85 percent / N-methylmorpholine N-oxide monohydrate / OsO₄ / acetone; H₂O / 16 h / 20 °C

8.1: NaH / tetrahydrofuran / 2 h / 20 °C

8.2: 72 percent / HMPA / tetrahydrofuran / 12 h / 20 °C

9.1: 82 percent / aq. acetic acid / 14 h / 20 °C

With dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; oxalyl dichloride; diphenyl diselenide; sodium hydride; acetic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; osmium(VIII) oxide; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; 1,2-dichloro-ethane; acetone; 1.1: Swern oxidation;
DOI:10.1021/jo061717t

Reference yield:

: 921771-14-4
(1S,4S,5R)-5-[(2S)-1,4-dioxa-spiro[4.5]dec-2-yl]-cyclohex-2-ene-1,4-diol

: 921771-19-9
(S)-1-((1S,2R,3S,4R,5S)-2,3,4,5-Tetrakis-benzyloxy-cyclohexyl)-ethane-1,2-diol

Guidance literature:: Multi-step reaction with 4 steps

1.1: NaH / tetrahydrofuran / 2 h / 20 °C

1.2: 69 percent / HMPA / tetrahydrofuran / 12 h / 20 °C

2.1: 85 percent / N-methylmorpholine N-oxide monohydrate / OsO₄ / acetone; H₂O / 16 h / 20 °C

3.1: NaH / tetrahydrofuran / 2 h / 20 °C

3.2: 72 percent / HMPA / tetrahydrofuran / 12 h / 20 °C

4.1: 82 percent / aq. acetic acid / 14 h / 20 °C

With sodium hydride; acetic acid; 4-methylmorpholine N-oxide; osmium(VIII) oxide; In tetrahydrofuran; water; acetone;
DOI:10.1021/jo061717t