(S)-2-[(4R,5R,6S)-6-((R)-2-Hydroxy-1-methyl-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-thiopropionic acid S-phenyl ester

Base Information

Chemical Name:(S)-2-[(4R,5R,6S)-6-((R)-2-Hydroxy-1-methyl-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-thiopropionic acid S-phenyl ester
CAS No.:121587-27-7
Molecular Formula:C₁₉H₂₈O₄S
Molecular Weight:352.495
Hs Code.:

Synonyms:(S)-2-[(4R,5R,6S)-6-((R)-2-Hydroxy-1-methyl-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-thiopropionic acid S-phenyl ester

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Chemical Property of (S)-2-[(4R,5R,6S)-6-((R)-2-Hydroxy-1-methyl-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-thiopropionic acid S-phenyl ester

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Technology Process of (S)-2-[(4R,5R,6S)-6-((R)-2-Hydroxy-1-methyl-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-thiopropionic acid S-phenyl ester

There total 8 articles about (S)-2-[(4R,5R,6S)-6-((R)-2-Hydroxy-1-methyl-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-thiopropionic acid S-phenyl ester 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: 79.0%

: 96481-70-8
(+)-(2S,3R,4R,5S,6R)-S-phenyl 3,5,7-trihydroxy-2,4,6-trimethylthioheptanoate 5,7-acetonide

: 121587-27-7
(S)-2-[(4R,5R,6S)-6-((R)-2-Hydroxy-1-methyl-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-thiopropionic acid S-phenyl ester

Guidance literature:: With toluene-4-sulfonic acid; 2,2-dimethoxy-propane; In acetonitrile;
DOI:10.1016/S0040-4039(00)82346-1

Reference yield: 62.0%

: 96481-70-8
(+)-(2S,3R,4S,5S,6R)-S-Phenyl 3-Hydroxy-5,7-(isopropylidenedioxy)-2,4,6-trimethylheptanethioate

: 77-76-9
2,2-dimethoxy-propane

: 121587-27-7
(+)-(2S,3R,4R,5S,6R)-S-Phenyl 7-Hydroxy-3,5-(isopropylidenedioxy)-2,4,6-trimethylheptanethioate

Guidance literature:: With pyridinium p-toluenesulfonate; In acetonitrile; Ambient temperature;
DOI:10.1002/hlca.19900730203

Reference yield:

: 40955-11-1,40955-12-2,40955-13-3
(2S,3S,4R)-3-Hydroxy-2,4-dimethyl-pentanedioic acid dimethyl ester

: 121587-27-7
(S)-2-[(4R,5R,6S)-6-((R)-2-Hydroxy-1-methyl-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-thiopropionic acid S-phenyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: pig liver esterase / pH = 6.8, phosphate buffer

2: 69 percent / BH₃*SMe₂ / tetrahydrofuran

3: 69 percent / amberlyst

4: 85 percent / DIBAL-H / toluene / -90 °C

5: 2.) H₂O₂ / 1.) Et₂O, - 80 deg C

6: 79 percent / TsOH, Me₂C(OMe)2 / acetonitrile

With pig liver esterase; dimethylsulfide borane complex; Amberlyst; dihydrogen peroxide; diisobutylaluminium hydride; toluene-4-sulfonic acid; 2,2-dimethoxy-propane; In tetrahydrofuran; toluene; acetonitrile;
DOI:10.1016/S0040-4039(00)82346-1