(2S,3R,4S)-N-(p-tolylsulfonyl)-3,4-dihydroxyproline-3,4-isopropylidene acetal methyl ester

Base Information

• Chemical Name: (2S,3R,4S)-N-(p-tolylsulfonyl)-3,4-dihydroxyproline-3,4-isopropylidene acetal methyl ester
• CAS No.: 160797-25-1
• Molecular Formula: C₁₆H₂₁NO₆S
• Molecular Weight: 355.412
• Mol file: 160797-25-1.mol

Synonyms:(2S,3R,4S)-N-(p-tolylsulfonyl)-3,4-dihydroxyproline-3,4-isopropylidene acetal methyl ester

Chemical Property of (2S,3R,4S)-N-(p-tolylsulfonyl)-3,4-dihydroxyproline-3,4-isopropylidene acetal methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4S)-N-(p-tolylsulfonyl)-3,4-dihydroxyproline-3,4-isopropylidene acetal methyl ester

There total 1 articles about (2S,3R,4S)-N-(p-tolylsulfonyl)-3,4-dihydroxyproline-3,4-isopropylidene acetal methyl 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:

(S)-3,4-Dihydroxy-1-(toluene-4-sulfonyl)-pyrrolidine-2-carboxylic acid methyl ester (17645-35-1,17645-36-2,57918-33-9,57918-34-0,79812-79-6,145985-02-0) + 2,2-dimethoxy-propane (77-76-9) → (2S,3S,4R)-N-(p-tolylsulfonyl)-3,4-dihydroxyproline-3,4-isopropylidene acetal methyl ester + (2S,3R,4S)-N-(p-tolylsulfonyl)-3,4-dihydroxyproline-3,4-isopropylidene acetal methyl ester (160797-25-1)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; for 18h;

DOI:10.1016/0008-6215(94)84059-8

Reference yield: 79.0%

(2S,3R,4S)-N-(p-tolylsulfonyl)-3,4-dihydroxyproline-3,4-isopropylidene acetal methyl ester (160797-25-1) → (2R,3R,4S)-1-(p-tolylsulfonyl)-2-hydroxymethylpyrrolidine-3,4-diol-3,4-isopropylidene acetal

Guidance literature:

With lithium borohydride; In tetrahydrofuran; for 4h;

DOI:10.1016/0008-6215(94)84059-8

Reference yield:

(2S,3R,4S)-N-(p-tolylsulfonyl)-3,4-dihydroxyproline-3,4-isopropylidene acetal methyl ester (160797-25-1) → (2R,3R,4S)-2-hydroxymethylpyrrolidine-3,4-diol (105990-41-8,186759-56-8,187339-50-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 79 percent / LiBH₄ / tetrahydrofuran / 4 h

2: sodium naphthalenide / tetrahydrofuran / -78 °C

With lithium borohydride; sodium naphthalenide; In tetrahydrofuran;

DOI:10.1016/0008-6215(94)84059-8

upstream raw materials:

(S)-3,4-Dihydroxy-1-(toluene-4-sulfonyl)-pyrrolidine-2-carboxylic acid methyl ester

2,2-dimethoxy-propane

Downstream raw materials:

(2R,3R,4S)-2-hydroxymethylpyrrolidine-3,4-diol