(1S,2R,3S,4S,5S,6R)-3,4,5-Tris-benzyloxy-6-(4-methoxy-benzyloxy)-cyclohexane-1,2-diol

Base Information

Chemical Name:(1S,2R,3S,4S,5S,6R)-3,4,5-Tris-benzyloxy-6-(4-methoxy-benzyloxy)-cyclohexane-1,2-diol
CAS No.:898808-38-3
Molecular Formula:C₃₅H₃₈O₇
Molecular Weight:570.683
Hs Code.:

Synonyms:(1S,2R,3S,4S,5S,6R)-3,4,5-Tris-benzyloxy-6-(4-methoxy-benzyloxy)-cyclohexane-1,2-diol

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Chemical Property of (1S,2R,3S,4S,5S,6R)-3,4,5-Tris-benzyloxy-6-(4-methoxy-benzyloxy)-cyclohexane-1,2-diol

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Technology Process of (1S,2R,3S,4S,5S,6R)-3,4,5-Tris-benzyloxy-6-(4-methoxy-benzyloxy)-cyclohexane-1,2-diol

There total 3 articles about (1S,2R,3S,4S,5S,6R)-3,4,5-Tris-benzyloxy-6-(4-methoxy-benzyloxy)-cyclohexane-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: 43.0%

: 898808-37-2
(2R,3S,4S,5S)-2,3,4-Tris-benzyloxy-5-(4-methoxy-benzyloxy)-hexane-1,6-diol

: 898808-38-3
(1S,2R,3S,4S,5S,6R)-3,4,5-Tris-benzyloxy-6-(4-methoxy-benzyloxy)-cyclohexane-1,2-diol

Guidance literature:: (2R,3S,4S,5S)-2,3,4-Tris-benzyloxy-5-(4-methoxy-benzyloxy)-hexane-1,6-diol; With oxalyl dichloride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at -78 - 20 ℃; for 3h;

With samarium diiodide; tert-butyl alcohol; In tetrahydrofuran; at -78 ℃; for 3.5h;
DOI:10.1016/j.carres.2006.03.031

Reference yield:

: 898808-33-8
2,3,4-tri-O-benzyl-1,6-bis-O-(tert-butyldimethylsilyl)hexane-1,2,3,4,5,6-hexaol

: 898808-38-3
(1S,2R,3S,4S,5S,6R)-3,4,5-Tris-benzyloxy-6-(4-methoxy-benzyloxy)-cyclohexane-1,2-diol

Guidance literature:: Multi-step reaction with 3 steps

1.1: NaH / tetrahydrofuran / 1 h / 20 °C

1.2: TBAI / tetrahydrofuran / 72 h / 20 °C

2.1: 183 mg / TBAF / tetrahydrofuran / 2 h / 20 °C

3.1: (COCl)2; DMSO; iPr₂EtNH / tetrahydrofuran / 3 h / -78 - 20 °C

3.2: 43 percent / tBuOH; SmI₂ / tetrahydrofuran / 3.5 h / -78 °C

With oxalyl dichloride; tetrabutyl ammonium fluoride; sodium hydride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 3.1: Swern oxidation;
DOI:10.1016/j.carres.2006.03.031

Reference yield:

: 1-Methoxy-4-[(1R,2S,3S,4S)-2,3,4-tris-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-pentyloxymethyl]-benzene

: 898808-38-3
(1S,2R,3S,4S,5S,6R)-3,4,5-Tris-benzyloxy-6-(4-methoxy-benzyloxy)-cyclohexane-1,2-diol

Guidance literature:: Multi-step reaction with 2 steps

1.1: 183 mg / TBAF / tetrahydrofuran / 2 h / 20 °C

2.1: (COCl)2; DMSO; iPr₂EtNH / tetrahydrofuran / 3 h / -78 - 20 °C

2.2: 43 percent / tBuOH; SmI₂ / tetrahydrofuran / 3.5 h / -78 °C

With oxalyl dichloride; tetrabutyl ammonium fluoride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 2.1: Swern oxidation;
DOI:10.1016/j.carres.2006.03.031