2-epi-Validamine

Base Information

• Chemical Name: 2-epi-Validamine
• CAS No.: 191740-46-2
• Molecular Formula: C₇H₁₅NO₄
• Molecular Weight: 177.2
• Mol file: 191740-46-2.mol

Synonyms:2-epi-Validamine

Chemical Property of 2-epi-Validamine

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-epi-Validamine

There total 6 articles about 2-epi-Validamine 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:

3-O-acetyl 4,6-O-benzylidene-N-benzyloxycarbonyl-2-O-(p-tolylsulfonyl)-5a-carba-D-glucopyranosylamine → validamine (32780-32-8) + 2-epi-Validamine (191740-46-2)

Guidance literature:

With hydrogenchloride; sodium benzoate; barium dihydroxide; Yield given. Multistep reaction; 1) DMF, 140 deg C, 120 h, 2) MeOH, reflux, 30 min, 3) H₂O, 80 deg C, 4 h;

DOI:10.1016/S0008-6215(97)00052-9

Reference yield:

(1R,2R,3S,4R,5R)-3,4-di-O-benzyl-5-benzyloxymethyl-1,2-O,O-sulfonyl-cyclohexane-1,2,3,4-tetraol (151693-59-3) → 2-epi-Validamine (191740-46-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) LiN₃, 2.) aq. H₂SO₄ / 1.) DMF, 105 deg C, 2.5 h, 2.) THF, 50 deg C, 30 min

2: H₂ / Raney nickel / ethyl acetate / 18 h / Ambient temperature

3: Na, NH₃ / 1.5 h / -40 °C

With lithium azide; sulfuric acid; ammonia; hydrogen; sodium; nickel; In ethyl acetate;

DOI:10.1021/jo00121a065

Reference yield:

(1R,2R,3R,4S,6R)-4-Azido-1,2-di-O-benzyl-6-<(benzyloxy)methyl>-1,2,3-cyclohexanetriol (166376-48-3) → 2-epi-Validamine (191740-46-2)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / Raney nickel / ethyl acetate / 18 h / Ambient temperature

2: Na, NH₃ / 1.5 h / -40 °C

With ammonia; hydrogen; sodium; nickel; In ethyl acetate;

DOI:10.1021/jo00121a065

upstream raw materials:

(1R)-(1,3,4/2,6)-1,7-O-benzylidene-4-<(benzyloxycarbonyl)amino>-6-C-(hydroxymethyl)-1,2,3-cyclohexanetriol

(1R,2R,3S,4R,5R)-3,4-di-O-benzyl-5-benzyloxymethyl-1,2-O,O-sulfonyl-cyclohexane-1,2,3,4-tetraol

(1R,2R,3R,4S,6R)-4-Azido-1,2-di-O-benzyl-6-<(benzyloxy)methyl>-1,2,3-cyclohexanetriol

Downstream raw materials:

acetic acid (1R,2S,3R,4S,6R)-2,3-diacetoxy-6-acetoxymethyl-4-acetylaminocyclohexyl ester