(3R,4R,5R,6R)-3-Azido-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenyl-tetrahydro-pyran-2-ol

Base Information

• Chemical Name: (3R,4R,5R,6R)-3-Azido-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenyl-tetrahydro-pyran-2-ol
• CAS No.: 175981-95-0
• Molecular Formula: C₃₃H₃₃N₃O₅
• Molecular Weight: 551.642
• Mol file: 175981-95-0.mol

Synonyms:(3R,4R,5R,6R)-3-Azido-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenyl-tetrahydro-pyran-2-ol

Chemical Property of (3R,4R,5R,6R)-3-Azido-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenyl-tetrahydro-pyran-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4R,5R,6R)-3-Azido-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenyl-tetrahydro-pyran-2-ol

There total 1 articles about (3R,4R,5R,6R)-3-Azido-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenyl-tetrahydro-pyran-2-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: 85.4%

phenyllithium (591-51-5) + (3R,4R,5R,6R)-3-azido-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one (160701-84-8) → (3R,4R,5R,6R)-3-Azido-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenyl-tetrahydro-pyran-2-ol (175981-95-0)

Guidance literature:

In toluene; at -78 ℃; for 1h;

DOI:10.1039/CC9960000347

Reference yield: 91.0%

(3R,4R,5R,6R)-3-Azido-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenyl-tetrahydro-pyran-2-ol (175981-95-0) → (2S,3S,4R,5R,6R)-3-Azido-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenyl-tetrahydro-pyran (175982-00-0)

Guidance literature:

With triethylsilane; boron trifluoride diethyl etherate; In acetonitrile; at -40 ℃; for 0.25h;

DOI:10.1039/CC9960000347

Reference yield:

(3R,4R,5R,6R)-3-Azido-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenyl-tetrahydro-pyran-2-ol (175981-95-0) → Acetic acid (2R,3R,4R,5S,6S)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-phenyl-tetrahydro-pyran-4-yl ester

Guidance literature:

Multi-step reaction with 4 steps

1: 91 percent / Et₃SiH, BF₃*Et₂O / acetonitrile / 0.25 h / -40 °C

2: 75 percent / H₂ / Raney Ni

3: 89 percent / H₂ / Pd/C / tetrahydrofuran

4: 91 percent

With triethylsilane; boron trifluoride diethyl etherate; hydrogen; palladium on activated charcoal; nickel; In tetrahydrofuran; acetonitrile;

DOI:10.1039/CC9960000347

upstream raw materials:

phenyllithium

(3R,4R,5R,6R)-3-azido-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

Downstream raw materials:

(2S,3S,4R,5R,6R)-3-Azido-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenyl-tetrahydro-pyran

N-((2S,3R,4R,5R,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-phenyl-tetrahydro-pyran-3-yl)-acetamide

N-((2S,3S,4R,5S,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-phenyltetrahydro-2H-pyran-3-yl)acetamide