(2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->6)-1-O-allyl-2,3,4,5-tetra-O-benzyl-D-myo-inositol

Base Information

• Chemical Name: (2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->6)-1-O-allyl-2,3,4,5-tetra-O-benzyl-D-myo-inositol
• CAS No.: 150772-66-0
• Molecular Formula: C₅₇H₆₁N₃O₁₀
• Molecular Weight: 948.125
• Mol file: 150772-66-0.mol

Synonyms:(2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->6)-1-O-allyl-2,3,4,5-tetra-O-benzyl-D-myo-inositol

Chemical Property of (2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->6)-1-O-allyl-2,3,4,5-tetra-O-benzyl-D-myo-inositol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->6)-1-O-allyl-2,3,4,5-tetra-O-benzyl-D-myo-inositol

There total 33 articles about (2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->6)-1-O-allyl-2,3,4,5-tetra-O-benzyl-D-myo-inositol 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%

1-O-Allyl-2,3,4,5-tetra-O-benzyl-6-O-(2-azido-3,6-di-O-benzyl-4-O-tert-butylmethylsilyl-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol (260392-75-4) → (2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->6)-1-O-allyl-2,3,4,5-tetra-O-benzyl-D-myo-inositol (150772-66-0)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran;

DOI:10.1002/(SICI)1521-3773(19981231)37:24<3423::AID-ANIE3423>3.0.CO;2-I

Reference yield: 86.0%

(2-azido-3-O-benzyl-4,6-benzylidene-2-deoxy-α-D-glucopyranosyl)-(1->6)-1-O-allyl-2,3,4,5-tetra-O-benzyl-D-myo-inositol → (2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->6)-1-O-allyl-2,3,4,5-tetra-O-benzyl-D-myo-inositol (150772-66-0)

Guidance literature:

With hydrogenchloride; sodium cyanoborohydride; In tetrahydrofuran; diethyl ether; at 0 - 20 ℃; for 2h; pH=1;

DOI:10.1016/j.bioorg.2010.12.002

Reference yield:

1-O-allyl-2,3,4,5-tetra-O-benzyl-D-myo-inositol (132437-54-8) → (2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->6)-1-O-allyl-2,3,4,5-tetra-O-benzyl-D-myo-inositol (150772-66-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 65 percent / TBABr; molecular sieves 4 Angstroem / CH₂Cl₂ / 24 h / 20 °C

2: 88 percent / TBAF / tetrahydrofuran / 2 h / 20 °C

With 4 A molecular sieve; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; In tetrahydrofuran; dichloromethane; 1: Etherification / 2: Desilylation;

upstream raw materials:

1-O-Allyl-2,3,4,5-tetra-O-benzyl-6-O-(2-azido-3,6-di-O-benzyl-4-O-tert-butylmethylsilyl-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol

ethyl 4,6-O-benzylidene-2-deoxy-2-N-phthalamido-1-thio-β-Dglucopyranoside

benzyl bromide

1-O-allyl-2,3,4,5-tetra-O-benzyl-D-myo-inositol

Downstream raw materials:

O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->6)-1-O-allyl-2,3,4,5-tetra-O-benzyl-D-myo-inositol

O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->6)-2,3,4,5-tetra-O-benzyl-D-myo-inositol

O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl)-(1-4)-O-(2-O-acetyl-3-O-benzyl-6-O-(chloroacetyl)-α-D-mannopyranosyl)-(1-4)-O-(2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1-6)-1-O-allyl-2,3,4,5-tetra-O-benzyl-D-myo-inosito