methyl (2R,3S)-3,4-O-isopropylidene-2,3,4-trihydroxy-2-O-(p-toluenesulfonyl)butanoate

Base Information

• Chemical Name: methyl (2R,3S)-3,4-O-isopropylidene-2,3,4-trihydroxy-2-O-(p-toluenesulfonyl)butanoate
• CAS No.: 166249-17-8
• Molecular Formula: C₁₅H₂₀O₇S
• Molecular Weight: 344.386
• Mol file: 166249-17-8.mol

Synonyms:methyl (2R,3S)-3,4-O-isopropylidene-2,3,4-trihydroxy-2-O-(p-toluenesulfonyl)butanoate

Chemical Property of methyl (2R,3S)-3,4-O-isopropylidene-2,3,4-trihydroxy-2-O-(p-toluenesulfonyl)butanoate

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (2R,3S)-3,4-O-isopropylidene-2,3,4-trihydroxy-2-O-(p-toluenesulfonyl)butanoate

There total 4 articles about methyl (2R,3S)-3,4-O-isopropylidene-2,3,4-trihydroxy-2-O-(p-toluenesulfonyl)butanoate 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: 95.0%

p-toluenesulfonyl chloride (98-59-9) + methyl (2R,3S)-3,4-O-isopropylidene-2,3,4-trihydroxybutanoate (92973-40-5) → methyl (2R,3S)-3,4-O-isopropylidene-2,3,4-trihydroxy-2-O-(p-toluenesulfonyl)butanoate (166249-17-8)

Guidance literature:

With pyridine; In dichloromethane; at 0 ℃; for 10h;

DOI:10.1016/j.tet.2005.03.001

Reference yield:

5,6-O-isopropylidene-L-ascorbic acid (15042-01-0) → methyl (2R,3S)-3,4-O-isopropylidene-2,3,4-trihydroxy-2-O-(p-toluenesulfonyl)butanoate (166249-17-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaOH; NaHCO₃; hydrogen peroxide / H₂O / 1 h / 20 °C

1.2: 78 percent / sodium sulfite; NaHCO₃ / H₂O / 4 h / 40 °C

2.1: 95 percent / pyridine / CH₂Cl₂ / 10 h / 0 °C

With pyridine; sodium hydroxide; dihydrogen peroxide; sodium hydrogencarbonate; In dichloromethane; water;

DOI:10.1016/j.tet.2005.03.001

Reference yield:

O3,O4-(1-methylethylidene)-L-threonic acid (92973-39-2,136136-17-9) → methyl (2R,3S)-3,4-O-isopropylidene-2,3,4-trihydroxy-2-O-(p-toluenesulfonyl)butanoate (166249-17-8)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydrogencarbonate / water; 1-methyl-pyrrolidin-2-one / 3 h / 35 - 60 °C / Large scale

2: triethylamine; dmap / acetonitrile / 3.5 h / 25 °C / Large scale

With dmap; sodium hydrogencarbonate; triethylamine; In 1-methyl-pyrrolidin-2-one; water; acetonitrile;

upstream raw materials:

p-toluenesulfonyl chloride

methyl (2R,3S)-3,4-O-isopropylidene-2,3,4-trihydroxybutanoate

5,6-O-isopropylidene-L-ascorbic acid

(2R)-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl](hydroxy)ethanoic acid sodium salt

Downstream raw materials:

(S)-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-hydroxyethyl 4-methylbenzenesulfonate

(2S,3R)-3,4-epoxy-1,2-O-isopropylidenebutane-1,2-diol

(2R,3S)-1,2-O-isopropylidene-3-(t-butoxycarbonyl)amino-4-phenybutane-1,2-diol

4-chloro-6-((R)-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)ethoxy)-2-(4-fluorobenzylthio)pyrimidine