(2S,3R,4R,5S)-2,5-Diazido-1,6-bis-benzyloxy-hexane-3,4-diol

Base Information

• Chemical Name: (2S,3R,4R,5S)-2,5-Diazido-1,6-bis-benzyloxy-hexane-3,4-diol
• CAS No.: 505084-92-4
• Molecular Formula: C₂₀H₂₄N₆O₄
• Molecular Weight: 412.448
• Mol file: 505084-92-4.mol

Synonyms:(2S,3R,4R,5S)-2,5-Diazido-1,6-bis-benzyloxy-hexane-3,4-diol

Chemical Property of (2S,3R,4R,5S)-2,5-Diazido-1,6-bis-benzyloxy-hexane-3,4-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4R,5S)-2,5-Diazido-1,6-bis-benzyloxy-hexane-3,4-diol

There total 1 articles about (2S,3R,4R,5S)-2,5-Diazido-1,6-bis-benzyloxy-hexane-3,4-diol 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: 85.0%

3,5-diazido-1,6-di-O-benzyl-2,5-dideoxy-3,4-O-methylethylidene-L-iditol (142285-65-2) → (2S,3R,4R,5S)-2,5-Diazido-1,6-bis-benzyloxy-hexane-3,4-diol (505084-92-4)

Guidance literature:

With camphor-10-sulfonic acid; In methanol; for 24h; Heating;

DOI:10.1016/j.tetlet.2005.03.038

Reference yield: 93.0%

di-tert-butyl dicarbonate (24424-99-5) + (2S,3R,4R,5S)-2,5-Diazido-1,6-bis-benzyloxy-hexane-3,4-diol (505084-92-4) → (5-benzyloxy-1-benzyloxymethyl-4-tert-butoxycarbonylamino-2,3-dihydroxy-pentyl)-carbamic acid tert-butyl ester (505085-04-1)

Guidance literature:

With hydrogen; Lindlar's catalyst; In methanol; at 20 ℃; for 2h;

DOI:10.1016/j.tetlet.2005.03.038

Reference yield:

(2S,3R,4R,5S)-2,5-Diazido-1,6-bis-benzyloxy-hexane-3,4-diol (505084-92-4) → N-(tert-butyloxycarbonyl)-O-benzyl-L-serinol (79069-15-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 93 percent / H₂ / Lindlar's catalyst / methanol / 2 h / 20 °C

2: 93 percent / NaIO₄/SiO₂ / CH₂Cl₂ / 2 h / 20 °C

3: 92 percent / NaBH₄ / methanol / -20 °C

With sodium tetrahydroborate; sodium periodate; hydrogen; silica gel; Lindlar's catalyst; In methanol; dichloromethane;

DOI:10.1016/j.tetlet.2005.03.038

upstream raw materials:

3,5-diazido-1,6-di-O-benzyl-2,5-dideoxy-3,4-O-methylethylidene-L-iditol

Downstream raw materials:

(5-benzyloxy-1-benzyloxymethyl-4-tert-butoxycarbonylamino-2,3-dihydroxy-pentyl)-carbamic acid tert-butyl ester

N-(tert-butyloxycarbonyl)-O-benzyl-L-serinol