(2S,4R)-4-((2S,3R,4S,5R,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

Base Information

• Chemical Name: (2S,4R)-4-((2S,3R,4S,5R,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester
• CAS No.: 122350-62-3
• Molecular Formula: C₂₈H₃₅NO₁₄
• Molecular Weight: 609.584
• Mol file: 122350-62-3.mol

Synonyms:

Chemical Property of (2S,4R)-4-((2S,3R,4S,5R,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4R)-4-((2S,3R,4S,5R,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

There total 2 articles about (2S,4R)-4-((2S,3R,4S,5R,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-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: 40.0%

methyl (2S,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylate (64187-48-0) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → (2S,4R)-4-((2R,3R,4S,5R,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester (122350-62-3,122407-76-5,124151-30-0) + (2S,4R)-4-((2S,3R,4S,5R,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester (122350-62-3,122407-76-5,124151-30-0)

Guidance literature:

With mercury(II) cyanide; In nitromethane; benzene; at 80 ℃; for 4h;

DOI:10.1016/S0040-4020(01)89802-1

Reference yield: 40.0%

methyl (2S,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylate (64187-48-0) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → (2S,4R)-4-((2R,3R,4S,5R,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester (122350-62-3,122407-76-5,124151-30-0) + (2S,4R)-4-((2S,3R,4S,5R,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester (122350-62-3,122407-76-5,124151-30-0)

Guidance literature:

With mercury(II) cyanide; In nitromethane; benzene; at 80 ℃; for 4h;

DOI:10.1016/S0040-4020(01)89802-1

Reference yield:

(2S,4R)-4-((2R,3R,4S,5R,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester (122350-62-3,122407-76-5,124151-30-0) → Boc-Tyr-DMet-Gly-Phe-1-2,3,4,6-tetra-O-acetyl-β-glcp> Hyp-OMe (122350-65-6,124151-31-1)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogen / 10percent palladium on charcoal / methanol

2: 75 percent / 1-hydroxybenzotriazole, N,N-dicyclohexylcarbodiimide / tetrahydrofuran / -15 deg C, 1 h then R_.T_., overnight

With hydrogen; benzotriazol-1-ol; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; methanol;

DOI:10.1016/S0040-4020(01)89802-1

upstream raw materials:

methyl (2S,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylate

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

Downstream raw materials:

Boc-Tyr-DMet-Gly-Phe-1-2,3,4,6-tetra-O-acetyl-β-glcp> Hyp-OMe