(S)-2-[2-((2S,3R,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-acetylamino]-pentanedioic acid dibenzyl ester

Base Information

• Chemical Name: (S)-2-[2-((2S,3R,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-acetylamino]-pentanedioic acid dibenzyl ester
• CAS No.: 330955-09-4
• Molecular Formula: C₄₈H₅₁NO₁₀
• Molecular Weight: 801.934
• Mol file: 330955-09-4.mol

Synonyms:

Chemical Property of (S)-2-[2-((2S,3R,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-acetylamino]-pentanedioic acid dibenzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-[2-((2S,3R,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-acetylamino]-pentanedioic acid dibenzyl ester

There total 4 articles about (S)-2-[2-((2S,3R,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-acetylamino]-pentanedioic acid dibenzyl 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%

L-glutamic acid dibenzyl ester 4-toluenesulfonate (2791-84-6,227205-81-4) + ((2S,3R,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-acetic acid (330955-08-3) → (S)-2-[2-((2S,3R,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-acetylamino]-pentanedioic acid dibenzyl ester (330955-09-4)

Guidance literature:

With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane;

DOI:10.1016/S0960-894X(00)00623-5

Reference yield:

2,3,4,6-tetra-O-benzyl-D-mannopyranose (4132-28-9,4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5) → (S)-2-[2-((2S,3R,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-acetylamino]-pentanedioic acid dibenzyl ester (330955-09-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: NaH

1.2: 75 percent / NaH / 0 °C

2.1: TMSOTf

3.1: NaOH

4.1: 40 percent / EDCI; Et₃N / CH₂Cl₂

With sodium hydroxide; trimethylsilyl trifluoromethanesulfonate; sodium hydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane;

DOI:10.1016/S0960-894X(00)00623-5

Reference yield:

methyl 2-(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)acetate (124813-80-5) → (S)-2-[2-((2S,3R,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-acetylamino]-pentanedioic acid dibenzyl ester (330955-09-4)

Guidance literature:

Multi-step reaction with 3 steps

1: TMSOTf

2: NaOH

3: 40 percent / EDCI; Et₃N / CH₂Cl₂

With sodium hydroxide; trimethylsilyl trifluoromethanesulfonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane;

DOI:10.1016/S0960-894X(00)00623-5

upstream raw materials:

L-glutamic acid dibenzyl ester 4-toluenesulfonate

((2S,3R,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-acetic acid

2,3,4,6-tetra-O-benzyl-D-mannopyranose

methyl 2-(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)acetate

Downstream raw materials:

(S)-2-[2-((2S,3R,4R,5S,6S)-3,4,5-Tris-benzyloxy-6-formyl-tetrahydro-pyran-2-yl)-acetylamino]-pentanedioic acid dibenzyl ester