Acetic acid (4R,5R,6S)-2,2,5-trimethyl-6-phenylsulfanylmethyl-[1,3]dioxan-4-ylmethyl ester

Base Information

Chemical Name:Acetic acid (4R,5R,6S)-2,2,5-trimethyl-6-phenylsulfanylmethyl-[1,3]dioxan-4-ylmethyl ester
CAS No.:193890-11-8
Molecular Formula:C₁₇H₂₄O₄S
Molecular Weight:324.441
Hs Code.:

Synonyms:Acetic acid (4R,5R,6S)-2,2,5-trimethyl-6-phenylsulfanylmethyl-[1,3]dioxan-4-ylmethyl ester

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Chemical Property of Acetic acid (4R,5R,6S)-2,2,5-trimethyl-6-phenylsulfanylmethyl-[1,3]dioxan-4-ylmethyl ester

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Technology Process of Acetic acid (4R,5R,6S)-2,2,5-trimethyl-6-phenylsulfanylmethyl-[1,3]dioxan-4-ylmethyl ester

There total 5 articles about Acetic acid (4R,5R,6S)-2,2,5-trimethyl-6-phenylsulfanylmethyl-[1,3]dioxan-4-ylmethyl 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: 89.0%

: 882-33-7
diphenyldisulfane

: 193890-10-7
(4R,5S,6S)-4-acetyloxymethyl-6-hydroxymethyl-2,2,5-trimethyl-1,3-dioxane

: 193890-11-8
Acetic acid (4R,5R,6S)-2,2,5-trimethyl-6-phenylsulfanylmethyl-[1,3]dioxan-4-ylmethyl ester

Guidance literature:: With tributylphosphine; In pyridine; for 20h; Ambient temperature;
DOI:10.1016/S0040-4020(97)00625-X

Reference yield:

: 106820-52-4
(2R,3R,4S)-5-[(tert-butyldiphenylsilyl)oxy]-2-hydroxy-3-methyl-4-pentanolide

: 193890-11-8
Acetic acid (4R,5R,6S)-2,2,5-trimethyl-6-phenylsulfanylmethyl-[1,3]dioxan-4-ylmethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: NaBH₄ / tetrahydrofuran; H₂O / 0 deg C, 30 min, rt, 2 h

2: 2,4,6-collidine / CH₂Cl₂ / 3 h / -78 - -30 °C

3: pyridinium p-toluenesulfonate / benzene; CH₂Cl₂ / 13.5 h / Ambient temperature

4: TBAF / tetrahydrofuran / 13 h / Ambient temperature

5: 89 percent / Bu₃P / pyridine / 20 h / Ambient temperature

With 2,4,6-trimethyl-pyridine; sodium tetrahydroborate; tributylphosphine; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; In tetrahydrofuran; pyridine; dichloromethane; water; benzene;
DOI:10.1016/S0040-4020(97)00625-X

Reference yield:

: 193952-78-2
(2R,3R,4S)-5-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-pentane-1,2,4-triol

: 193890-11-8
Acetic acid (4R,5R,6S)-2,2,5-trimethyl-6-phenylsulfanylmethyl-[1,3]dioxan-4-ylmethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 2,4,6-collidine / CH₂Cl₂ / 3 h / -78 - -30 °C

2: pyridinium p-toluenesulfonate / benzene; CH₂Cl₂ / 13.5 h / Ambient temperature

3: TBAF / tetrahydrofuran / 13 h / Ambient temperature

4: 89 percent / Bu₃P / pyridine / 20 h / Ambient temperature

With 2,4,6-trimethyl-pyridine; tributylphosphine; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; In tetrahydrofuran; pyridine; dichloromethane; benzene;
DOI:10.1016/S0040-4020(97)00625-X