1-O-(6'-azido-6'-deoxy-2',3',4'-tri-O-benzyl-α-D-glucopyranosyl)-3-O-(2''-azido-2''-deoxy-3'',4'',6''-tri-O-benzyl-α-D-glucopyranosyl)-4,6-diazido-cyclohexan-1,2,3-ol

Base Information

• Chemical Name: 1-O-(6'-azido-6'-deoxy-2',3',4'-tri-O-benzyl-α-D-glucopyranosyl)-3-O-(2''-azido-2''-deoxy-3'',4'',6''-tri-O-benzyl-α-D-glucopyranosyl)-4,6-diazido-cyclohexan-1,2,3-ol
• CAS No.: 864862-35-1
• Molecular Formula: C₆₀H₆₄N₁₂O₁₁
• Molecular Weight: 1129.24

Synonyms:

Chemical Property of 1-O-(6'-azido-6'-deoxy-2',3',4'-tri-O-benzyl-α-D-glucopyranosyl)-3-O-(2''-azido-2''-deoxy-3'',4'',6''-tri-O-benzyl-α-D-glucopyranosyl)-4,6-diazido-cyclohexan-1,2,3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of 1-O-(6'-azido-6'-deoxy-2',3',4'-tri-O-benzyl-α-D-glucopyranosyl)-3-O-(2''-azido-2''-deoxy-3'',4'',6''-tri-O-benzyl-α-D-glucopyranosyl)-4,6-diazido-cyclohexan-1,2,3-ol

There total 3 articles about 1-O-(6'-azido-6'-deoxy-2',3',4'-tri-O-benzyl-α-D-glucopyranosyl)-3-O-(2''-azido-2''-deoxy-3'',4'',6''-tri-O-benzyl-α-D-glucopyranosyl)-4,6-diazido-cyclohexan-1,2,3-ol 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:

(1α,2β,3α,4β,6β)-4,6-Diazido-1,2,3-cyclohexantriol-triacetat (90852-19-0,864862-01-1) → 1-O-(6'-azido-6'-deoxy-2',3',4'-tri-O-benzyl-α-D-glucopyranosyl)-3-O-(2''-azido-2''-deoxy-3'',4'',6''-tri-O-benzyl-α-D-glucopyranosyl)-4,6-diazido-cyclohexan-1,2,3-ol (864862-35-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 60 percent / Novozym 435 / toluene; various solvent(s) / pH 6.2

2: 65 percent / 4 Angstroem molecular sieves; N-iodosuccinimide; AgOTf / CH₂Cl₂ / 2 h / 0 °C

3: 65 percent / NaOMe / methanol / 18 h / 20 °C

4: 24 percent / 4 Angstroem molecular sieves; N-iodosuccinimide; AgOTf / CH₂Cl₂ / 2 h / 0 °C

With N-iodo-succinimide; Novozym 435; 4 A molecular sieve; sodium methylate; silver trifluoromethanesulfonate; In methanol; dichloromethane; toluene;

DOI:10.1039/b505865a

Reference yield:

[(1S,2S,3R,4S,6R)-2-acetoxy-4,6-diazido-3-hydroxy-cyclohexyl] acetate (236115-61-0) → 1-O-(6'-azido-6'-deoxy-2',3',4'-tri-O-benzyl-α-D-glucopyranosyl)-3-O-(2''-azido-2''-deoxy-3'',4'',6''-tri-O-benzyl-α-D-glucopyranosyl)-4,6-diazido-cyclohexan-1,2,3-ol (864862-35-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 65 percent / 4 Angstroem molecular sieves; N-iodosuccinimide; AgOTf / CH₂Cl₂ / 2 h / 0 °C

2: 65 percent / NaOMe / methanol / 18 h / 20 °C

3: 24 percent / 4 Angstroem molecular sieves; N-iodosuccinimide; AgOTf / CH₂Cl₂ / 2 h / 0 °C

With N-iodo-succinimide; 4 A molecular sieve; sodium methylate; silver trifluoromethanesulfonate; In methanol; dichloromethane;

DOI:10.1039/b505865a

Reference yield:

(1R,2S,3S,4R,6S)-1-O-(6'-azido-6'-deoxy-2',3',4'-tri-O-benzyl-α-D-glucopyranosyl)-2,3-diacetoxy-4,6-diazido-cyclohexanol (864862-14-6) → 1-O-(6'-azido-6'-deoxy-2',3',4'-tri-O-benzyl-α-D-glucopyranosyl)-3-O-(2''-azido-2''-deoxy-3'',4'',6''-tri-O-benzyl-α-D-glucopyranosyl)-4,6-diazido-cyclohexan-1,2,3-ol (864862-35-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 65 percent / NaOMe / methanol / 18 h / 20 °C

2: 24 percent / 4 Angstroem molecular sieves; N-iodosuccinimide; AgOTf / CH₂Cl₂ / 2 h / 0 °C

With N-iodo-succinimide; 4 A molecular sieve; sodium methylate; silver trifluoromethanesulfonate; In methanol; dichloromethane;

DOI:10.1039/b505865a

upstream raw materials:

(1α,2β,3α,4β,6β)-4,6-Diazido-1,2,3-cyclohexantriol-triacetat

[(1S,2S,3R,4S,6R)-2-acetoxy-4,6-diazido-3-hydroxy-cyclohexyl] acetate

(1R,2S,3S,4R,6S)-1-O-(6'-azido-6'-deoxy-2',3',4'-tri-O-benzyl-α-D-glucopyranosyl)-2,3-diacetoxy-4,6-diazido-cyclohexanol

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