ethyl 3,6-di-O-benzyl-4-O-chloroacetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: ethyl 3,6-di-O-benzyl-4-O-chloroacetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside
• CAS No.: 560129-48-8
• Molecular Formula: C₃₂H₃₂ClNO₇S
• Molecular Weight: 610.128
• Mol file: 560129-48-8.mol

Synonyms:ethyl 3,6-di-O-benzyl-4-O-chloroacetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Chemical Property of ethyl 3,6-di-O-benzyl-4-O-chloroacetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 3,6-di-O-benzyl-4-O-chloroacetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

There total 2 articles about ethyl 3,6-di-O-benzyl-4-O-chloroacetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 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%

ethyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (115533-35-2) + Chloroacetic anhydride (541-88-8) → ethyl 3,6-di-O-benzyl-4-O-chloroacetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (560129-48-8)

Guidance literature:

With pyridine; In dichloromethane; at 0 ℃;

DOI:10.1016/0040-4039(96)01394-9

Reference yield:

2-((6S,7R,8aS)-8-benzyloxy-6-ethylsulfanyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-isoindole-1,3-dione (129519-27-3) → ethyl 3,6-di-O-benzyl-4-O-chloroacetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (560129-48-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / Na(CN)BH₃, mol. sieves 4 Angstroem / tetrahydrofuran / 0 °C

2: 95 percent / pyridine / CH₂Cl₂ / 0 °C

With pyridine; 4 A molecular sieve; sodium cyanoborohydride; In tetrahydrofuran; dichloromethane;

DOI:10.1016/0040-4039(96)01394-9

Reference yield: 95.5%

ethyl 3,6-di-O-benzyl-4-O-chloroacetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (560129-48-8) → 3,6-di-O-benzyl-4-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl fluoride (182923-79-1)

Guidance literature:

With pyridine; N-Bromosuccinimide; hydrogen fluoride; In dichloromethane; at 0 ℃; for 0.333333h;

DOI:10.1002/chem.200390156

upstream raw materials:

ethyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Chloroacetic anhydride

2-((6S,7R,8aS)-8-benzyloxy-6-ethylsulfanyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-isoindole-1,3-dione

Downstream raw materials:

3,6-di-O-benzyl-4-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl fluoride

chloro-acetic acid 4-benzyloxy-2-benzyloxymethyl-6-[4,6-bis-benzyloxy-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(4-methoxy-phenoxymethyl)-tetrahydro-pyran-3-yloxy]-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-3-yl ester

chloro-acetic acid 4-benzyloxy-6-[4-benzyloxy-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-methoxy-2-(4-methoxy-phenoxymethyl)-tetrahydro-pyran-3-yloxy]-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-3-yl ester

chloro-acetic acid 4-benzyloxy-6-[4-benzyloxy-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy]-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-3-yl ester