(2'R,4S)-(-)-2'-(2,2-dimethyl-1,3-dioxolan-4-yl)-1'-tosyloxypropane

Base Information

• Chemical Name: (2'R,4S)-(-)-2'-(2,2-dimethyl-1,3-dioxolan-4-yl)-1'-tosyloxypropane
• CAS No.: 69515-55-5
• Molecular Formula: C₁₅H₂₂O₅S
• Molecular Weight: 314.403
• Mol file: 69515-55-5.mol

Synonyms:(2'R,4S)-(-)-2'-(2,2-dimethyl-1,3-dioxolan-4-yl)-1'-tosyloxypropane

Chemical Property of (2'R,4S)-(-)-2'-(2,2-dimethyl-1,3-dioxolan-4-yl)-1'-tosyloxypropane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2'R,4S)-(-)-2'-(2,2-dimethyl-1,3-dioxolan-4-yl)-1'-tosyloxypropane

There total 4 articles about (2'R,4S)-(-)-2'-(2,2-dimethyl-1,3-dioxolan-4-yl)-1'-tosyloxypropane 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: 92.0%

(2S,3R)-threo-3-methylbutane-1,2,4-triol 1,2-acetonide (69743-60-8) + p-toluenesulfonyl chloride (98-59-9) → (2'R,4S)-(-)-2'-(2,2-dimethyl-1,3-dioxolan-4-yl)-1'-tosyloxypropane (69515-55-5)

Guidance literature:

In pyridine; 1.) 0 deg C, 2h; 2.) r.t., 8 h;

DOI:10.1016/S0040-4020(01)85883-X

Reference yield:

(2S,3R)-threo-3-methylbutane-1,2,4-triol 1,2-acetonide 4-benzyl ether (78479-15-9) → (2'R,4S)-(-)-2'-(2,2-dimethyl-1,3-dioxolan-4-yl)-1'-tosyloxypropane (69515-55-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / H₂, NaHCO₃ / 10 percent Pd/C / ethanol; H₂O / Ambient temperature

2: 92 percent / pyridine / 1.) 0 deg C, 2h; 2.) r.t., 8 h

With hydrogen; sodium hydrogencarbonate; palladium on activated charcoal; In pyridine; ethanol; water;

DOI:10.1016/S0040-4020(01)85883-X

Reference yield:

(2'S,4S)-(+)-methyl-2'-(2,2-dimethyl-1,3-dioxolan-4-yl)-propanoate (112775-74-3) → (2'R,4S)-(-)-2'-(2,2-dimethyl-1,3-dioxolan-4-yl)-1'-tosyloxypropane (69515-55-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / LiAlH₄ / diethyl ether / 1 h / Ambient temperature

2: 90 percent / pyridine / 2 h / 0 °C

With pyridine; lithium aluminium tetrahydride; In diethyl ether;

DOI:10.1016/S0040-4020(01)86814-9

upstream raw materials:

(2S,3R)-threo-3-methylbutane-1,2,4-triol 1,2-acetonide

p-toluenesulfonyl chloride

(2S,3R)-threo-3-methylbutane-1,2,4-triol 1,2-acetonide 4-benzyl ether

(2'S,4S)-(+)-methyl-2'-(2,2-dimethyl-1,3-dioxolan-4-yl)-propanoate

Downstream raw materials:

(-)-α-multistriatin

(1S,2R,4R,5R)-5-ethyl-2-methyl-4-tosyloxymethyl-6,8-dioxabicyclo<3.2.1>octane