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

Base Information

Chemical Name:Methanesulfonic acid (4R,5R,6S)-2,2,5-trimethyl-6-phenylsulfanylmethyl-[1,3]dioxan-4-ylmethyl ester
CAS No.:193890-15-2
Molecular Formula:C₁₆H₂₄O₅S₂
Molecular Weight:360.496
Hs Code.:

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

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

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

There total 7 articles about Methanesulfonic 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: 78.0%

: 882-33-7
diphenyldisulfane

: 193890-14-1
(4R,5S,6S)-6-hydroxymethyl-4-methanesulfonyloxymethyl-2,2,5-trimethyl-1,3-dioxane

: 193890-15-2
Methanesulfonic acid (4R,5R,6S)-2,2,5-trimethyl-6-phenylsulfanylmethyl-[1,3]dioxan-4-ylmethyl ester

Guidance literature:: With tributylphosphine; In pyridine; for 40h; 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

: 193890-15-2
Methanesulfonic acid (4R,5R,6S)-2,2,5-trimethyl-6-phenylsulfanylmethyl-[1,3]dioxan-4-ylmethyl ester

Guidance literature:: Multi-step reaction with 7 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: K₂CO₃ / methanol / 2 h / Ambient temperature

5: 96 percent / Et₃N / CH₂Cl₂ / 0 deg C, 15 min, rt, 15 h

6: TBAF / tetrahydrofuran / 15 h / 0 °C

7: 78 percent / Bu₃P / pyridine / 40 h / Ambient temperature

With 2,4,6-trimethyl-pyridine; sodium tetrahydroborate; tributylphosphine; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; potassium carbonate; triethylamine; In tetrahydrofuran; pyridine; methanol; 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

: 193890-15-2
Methanesulfonic acid (4R,5R,6S)-2,2,5-trimethyl-6-phenylsulfanylmethyl-[1,3]dioxan-4-ylmethyl ester

Guidance literature:: Multi-step reaction with 6 steps

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

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

3: K₂CO₃ / methanol / 2 h / Ambient temperature

4: 96 percent / Et₃N / CH₂Cl₂ / 0 deg C, 15 min, rt, 15 h

5: TBAF / tetrahydrofuran / 15 h / 0 °C

6: 78 percent / Bu₃P / pyridine / 40 h / Ambient temperature

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