(2S,3R,4S,5R,6R)-O-benzyl-3,5-(isopropylidenedioxy)-2,4,6-trimethyl-7-(phenylthio)heptan-1-ol

Base Information

Chemical Name:(2S,3R,4S,5R,6R)-O-benzyl-3,5-(isopropylidenedioxy)-2,4,6-trimethyl-7-(phenylthio)heptan-1-ol
CAS No.:160691-50-9
Molecular Formula:C₂₆H₃₆O₃S
Molecular Weight:428.636
Hs Code.:

Synonyms:(2S,3R,4S,5R,6R)-O-benzyl-3,5-(isopropylidenedioxy)-2,4,6-trimethyl-7-(phenylthio)heptan-1-ol

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Chemical Property of (2S,3R,4S,5R,6R)-O-benzyl-3,5-(isopropylidenedioxy)-2,4,6-trimethyl-7-(phenylthio)heptan-1-ol

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Technology Process of (2S,3R,4S,5R,6R)-O-benzyl-3,5-(isopropylidenedioxy)-2,4,6-trimethyl-7-(phenylthio)heptan-1-ol

There total 6 articles about (2S,3R,4S,5R,6R)-O-benzyl-3,5-(isopropylidenedioxy)-2,4,6-trimethyl-7-(phenylthio)heptan-1-ol 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%

: 2973-86-6
lithium thiophenoxide

: 160691-36-1
(2S,3S,4S,5R,6S)-7-(benzyloxy)-3,5-(isopropylidenedioxy)-2,4,6-trimethylheptyl p-toluenesulfonate

: 160691-50-9
(2S,3R,4S,5R,6R)-O-benzyl-3,5-(isopropylidenedioxy)-2,4,6-trimethyl-7-(phenylthio)heptan-1-ol

Guidance literature:: In tetrahydrofuran; for 3.5h; Heating;
DOI:10.1021/ja00104a010

Reference yield:

: 116546-78-2
(S)-1-benzyloxy-2-methylpentan-3-one

: 160691-50-9
(2S,3R,4S,5R,6R)-O-benzyl-3,5-(isopropylidenedioxy)-2,4,6-trimethyl-7-(phenylthio)heptan-1-ol

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) Sn(OTf)2, Et₃N / 1.) CH₂Cl₂, -78 deg C, 2 h, 2.) CH₂Cl₂, -78 deg C, 1 h

2: 1.) (+)-(Ipc)2BOH, 2.) m-CPBA / 1.) Et₂O, RT, 2 h, 2.) Et₂O, RT, 1 h

3: 95 percent / Et₃N, DMAP / CH₂Cl₂ / 1.5 h / 20 °C

4: 92 percent / PPTS / CH₂Cl₂ / 15 h / 20 °C

5: 99 percent / tetrahydrofuran / 3.5 h / Heating

With dmap; tin(II) trifluoromethanesulfonate; B-hydroxydiisopinocampheylborane; pyridinium p-toluenesulfonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja00104a010

Reference yield:

: 140925-44-6
(2S,3S,4R,5R,6S)-7-(benzyloxy)-2,4,6-trimethyl-1,3,5-heptanetriol

: 160691-50-9
(2S,3R,4S,5R,6R)-O-benzyl-3,5-(isopropylidenedioxy)-2,4,6-trimethyl-7-(phenylthio)heptan-1-ol

Guidance literature:: Multi-step reaction with 3 steps

1: 95 percent / Et₃N, DMAP / CH₂Cl₂ / 1.5 h / 20 °C

2: 92 percent / PPTS / CH₂Cl₂ / 15 h / 20 °C

3: 99 percent / tetrahydrofuran / 3.5 h / Heating

With dmap; pyridinium p-toluenesulfonate; triethylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja00104a010