(1R)-2,3,4,6-tetra-O-benzyl-3'(S)-carboxymethyl-spiro[1,5-anhydro-D-glucitol-1,2'-oxirane]

Base Information

• Chemical Name: (1R)-2,3,4,6-tetra-O-benzyl-3'(S)-carboxymethyl-spiro[1,5-anhydro-D-glucitol-1,2'-oxirane]
• CAS No.: 883143-12-2
• Molecular Formula: C₃₇H₃₈O₈
• Molecular Weight: 610.704
• Mol file: 883143-12-2.mol

Synonyms:(1R)-2,3,4,6-tetra-O-benzyl-3'(S)-carboxymethyl-spiro[1,5-anhydro-D-glucitol-1,2'-oxirane]

Chemical Property of (1R)-2,3,4,6-tetra-O-benzyl-3'(S)-carboxymethyl-spiro[1,5-anhydro-D-glucitol-1,2'-oxirane]

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R)-2,3,4,6-tetra-O-benzyl-3'(S)-carboxymethyl-spiro[1,5-anhydro-D-glucitol-1,2'-oxirane]

There total 3 articles about (1R)-2,3,4,6-tetra-O-benzyl-3'(S)-carboxymethyl-spiro[1,5-anhydro-D-glucitol-1,2'-oxirane] 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: 82.0%

bromoacetic acid methyl ester (96-32-2) + D-Glucono-1,5-lactone (90-80-2,1335-57-5,4253-68-3) → (1R)-2,3,4,6-tetra-O-benzyl-3'(S)-carboxymethyl-spiro[1,5-anhydro-D-glucitol-1,2'-oxirane] (883143-12-2)

Guidance literature:

bromoacetic acid methyl ester; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.5h; Inert atmosphere;

D-Glucono-1,5-lactone; In tetrahydrofuran; at -78 - 20 ℃; Inert atmosphere;

DOI:10.1016/j.carres.2008.12.024

Reference yield: 80.0%

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one (13096-62-3) + bromoacetic acid methyl ester (96-32-2) → (1R)-2,3,4,6-tetra-O-benzyl-3'(S)-carboxymethyl-spiro[1,5-anhydro-D-glucitol-1,2'-oxirane] (883143-12-2)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 2h;

DOI:10.1055/s-2005-922768

Reference yield:

2,3,4,6-Tetra-O-benzyl-D-glucopyranose (4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5,4132-28-9) → (1R)-2,3,4,6-tetra-O-benzyl-3'(S)-carboxymethyl-spiro[1,5-anhydro-D-glucitol-1,2'-oxirane] (883143-12-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: pyridinium chlorochromate / dichloromethane

2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C

2.2: 1.42 h / 20 °C

With pyridinium chlorochromate; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane;

upstream raw materials:

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

bromoacetic acid methyl ester

D-Glucono-1,5-lactone

2,3,4,6-Tetra-O-benzyl-D-glucopyranose

Downstream raw materials:

methyl (2S)-hydroxy-2-(1-allyl-2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-ethanoate

methyl (2S)-hydroxy-2-(1-allyl-2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-ethanoate

C₄₁H₅₆N₄O₁₃

C₄₁H₅₇N₅O₁₂