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

Base Information

• Chemical Name: 3,6-di-O-benzyl-4-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl fluoride
• CAS No.: 182923-79-1
• Molecular Formula: C₃₀H₂₇ClFNO₇
• Molecular Weight: 567.998
• Mol file: 182923-79-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 3 articles about 3,6-di-O-benzyl-4-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl fluoride 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: 95.5%

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

Reference yield:

ethyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (115533-35-2) → 3,6-di-O-benzyl-4-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl fluoride (182923-79-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 93.2 percent / pyridine / CH₂Cl₂ / 0 °C

2: 95.5 percent / NBS; HF/pyridine / CH₂Cl₂ / 0.33 h / 0 °C

With pyridine; N-Bromosuccinimide; hydrogen fluoride; In dichloromethane;

DOI:10.1002/chem.200390156

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) → 3,6-di-O-benzyl-4-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl fluoride (182923-79-1)

Guidance literature:

Multi-step reaction with 3 steps

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

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

3: 91 percent / HF-pyridine, NBS / CH₂Cl₂ / 0 °C

With pyridine; N-Bromosuccinimide; 4 A molecular sieve; sodium cyanoborohydride; pyridine hydrogenfluoride; In tetrahydrofuran; dichloromethane;

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

upstream raw materials:

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

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

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:

O-(3,6-di-O-benzyl-4-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide

3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1→4)-3-O-benzyl-2-deoxy-6-O-(p-methoxyphenyl)-2-phthalimido-β-D-glucopyranosyl azide

O-(4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide

O-(3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide