(S,S)-2-(acetoxymethyl)-2-phenyl-4,5-bis(p-toluenesulfonyloxymethyl)-1,3-dioxolane

Base Information

• Chemical Name: (S,S)-2-(acetoxymethyl)-2-phenyl-4,5-bis(p-toluenesulfonyloxymethyl)-1,3-dioxolane
• CAS No.: 158835-59-7
• Molecular Formula: C₂₈H₃₀O₁₀S₂
• Molecular Weight: 590.672
• Mol file: 158835-59-7.mol

Synonyms:(S,S)-2-(acetoxymethyl)-2-phenyl-4,5-bis(p-toluenesulfonyloxymethyl)-1,3-dioxolane

Chemical Property of (S,S)-2-(acetoxymethyl)-2-phenyl-4,5-bis(p-toluenesulfonyloxymethyl)-1,3-dioxolane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S,S)-2-(acetoxymethyl)-2-phenyl-4,5-bis(p-toluenesulfonyloxymethyl)-1,3-dioxolane

There total 2 articles about (S,S)-2-(acetoxymethyl)-2-phenyl-4,5-bis(p-toluenesulfonyloxymethyl)-1,3-dioxolane 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: 70.0%

2-acetoxyacetophenone (2243-35-8) + (S,S)-2,3-bis(O-trimethylsilyl)-1,4-bisbutane-1,2,3,4-tetrol (158835-58-6) → (S,S)-2-(acetoxymethyl)-2-phenyl-4,5-bis(p-toluenesulfonyloxymethyl)-1,3-dioxolane (158835-59-7)

Guidance literature:

With perchloric acid; trimethylsilyl trifluoromethanesulfonate; In chloroform; for 8h; Ambient temperature;

DOI:10.1016/0040-4039(94)88078-6

Reference yield:

(2S,3S)-butane-1,4-diol bis[4-methylbenzenesulfonate] (57495-46-2,68138-99-8) → (S,S)-2-(acetoxymethyl)-2-phenyl-4,5-bis(p-toluenesulfonyloxymethyl)-1,3-dioxolane (158835-59-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / CH₂Cl₂ / Ambient temperature

2: 60 percent / TMSOTf / CHCl₃ / Ambient temperature

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; chloroform;

DOI:10.1016/0957-4166(95)00257-P

Reference yield: 80.0%

(S,S)-2-(acetoxymethyl)-2-phenyl-4,5-bis(p-toluenesulfonyloxymethyl)-1,3-dioxolane (158835-59-7) → (S,S)-2-(hydroxymethyl)-2-phenyl-4,5-bis(p-toluenesulfonyloxymethyl)-1,3-dioxolane (158835-61-1)

Guidance literature:

With sodium methylate; In methanol; for 12h; Ambient temperature;

DOI:10.1016/0040-4039(94)88078-6

upstream raw materials:

2-acetoxyacetophenone

(S,S)-2,3-bis(O-trimethylsilyl)-1,4-bisbutane-1,2,3,4-tetrol

(2S,3S)-butane-1,4-diol bis[4-methylbenzenesulfonate]

Downstream raw materials:

(S,S)-2-(hydroxymethyl)-2-phenyl-4,5-bis(p-toluenesulfonyloxymethyl)-1,3-dioxolane

(4S,5S,2'rac)-2-phenyl-2-<(tetrahydropyran-2'-yl)oxymethyl>-4,5-bis(p-toluenesulfonyloxymethyl)-1,3-dioxolane