6-azido-6-deoxy-2,3,3’,4,4’-Penta-O-benzyl-6’-O-tert-butyldiphenylsilylsucrose

Base Information

• Chemical Name: 6-azido-6-deoxy-2,3,3’,4,4’-Penta-O-benzyl-6’-O-tert-butyldiphenylsilylsucrose
• CAS No.: 1632073-37-0
• Molecular Formula: C₆₃H₆₉N₃O₁₀Si
• Molecular Weight: 1056.34

Synonyms:6-azido-6-deoxy-2,3,3’,4,4’-Penta-O-benzyl-6’-O-tert-butyldiphenylsilylsucrose

Chemical Property of 6-azido-6-deoxy-2,3,3’,4,4’-Penta-O-benzyl-6’-O-tert-butyldiphenylsilylsucrose

Chemical Property:

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Technology Process of 6-azido-6-deoxy-2,3,3’,4,4’-Penta-O-benzyl-6’-O-tert-butyldiphenylsilylsucrose

There total 2 articles about 6-azido-6-deoxy-2,3,3’,4,4’-Penta-O-benzyl-6’-O-tert-butyldiphenylsilylsucrose 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: 96.0%

2,3,3’,4,4’-penta-O-benzyl-6’-O-tert-butyldiphenylsilyl-6-O-deoxy-6-iodosucrose (1632073-34-7) → 6-azido-6-deoxy-2,3,3’,4,4’-Penta-O-benzyl-6’-O-tert-butyldiphenylsilylsucrose (1632073-37-0)

Guidance literature:

With sodium azide; tetrabutylammomium bromide; In N,N-dimethyl-formamide; at 80 ℃; for 2h;

DOI:10.1055/s-0033-1340180

Reference yield:

6'-O-(tert-butyldiphenyl)silyl-2,3,3',4,4'-penta-O-benzylsucrose (1326706-59-5) → 6-azido-6-deoxy-2,3,3’,4,4’-Penta-O-benzyl-6’-O-tert-butyldiphenylsilylsucrose (1632073-37-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triphenylphosphine / toluene / 0.33 h / Reflux

1.2: 2 h / Reflux

2.1: tetrabutylammomium bromide; sodium azide / N,N-dimethyl-formamide / 2 h / 80 °C

With sodium azide; tetrabutylammomium bromide; triphenylphosphine; In N,N-dimethyl-formamide; toluene;

DOI:10.1055/s-0033-1340180

Reference yield: 75.0%

6-azido-6-deoxy-2,3,3’,4,4’-Penta-O-benzyl-6’-O-tert-butyldiphenylsilylsucrose (1632073-37-0) + allyl bromide (106-95-6) → 6-azido-6-deoxy-2,3,3’,4,4’-penta-O-benzyl-6’-O-tert-butyldiphenylsilyl-1’-O-(prop-2-en-1-yl)sucrose (1632073-38-1)

Guidance literature:

With tetrabutylammomium bromide; sodium hydroxide; In water; toluene; at 20 ℃; for 10h;

DOI:10.1055/s-0033-1340180

upstream raw materials:

6'-O-(tert-butyldiphenyl)silyl-2,3,3',4,4'-penta-O-benzylsucrose

2,3,3’,4,4’-penta-O-benzyl-6’-O-tert-butyldiphenylsilyl-6-O-deoxy-6-iodosucrose

Downstream raw materials:

6-azido-6-deoxy-2,3,3’,4,4’-penta-O-benzyl-6’-O-tert-butyldiphenylsilyl-1’-O-(prop-2-en-1-yl)sucrose

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