(3S,4S,5S,6S)-Hexahydro-1H-azepine-3,4,5,6-tetrol

Base Information

• Chemical Name: (3S,4S,5S,6S)-Hexahydro-1H-azepine-3,4,5,6-tetrol
• CAS No.: 16647-61-3
• Molecular Formula: C₆H₁₃NO₄
• Molecular Weight: 163.174
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID00937201
• Nikkaji Number: J1.303.360I
• Wikidata: Q82913413
• Mol file: 16647-61-3.mol

Synonyms:16647-61-3;1H-Azepine-3,4,5,6-tetrol, hexahydro-, (3S,4R,5R,6S)-;(3S,4S,5S,6S)-AZEPANE-3,4,5,6-TETROL;(3S,4S,5S,6S)-HEXAHYDRO-1H-AZEPINE-3,4,5,6-TETROL;azepane-3,4,5,6-tetrol;DTXSID00937201;(3S)-Hexahydro-1H-azepine-3alpha,4alpha,5beta,6beta-tetrol

Chemical Property of (3S,4S,5S,6S)-Hexahydro-1H-azepine-3,4,5,6-tetrol

Chemical Property:

• PSA: 92.95000
• LogP: -2.63800
• XLogP3: -2.9
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 0
• Exact Mass: 163.08445790
• Heavy Atom Count: 11
• Complexity: 118

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(C(C(CN1)O)O)O)O
• Isomeric SMILES: C1[C@@H]([C@@H]([C@H]([C@H](CN1)O)O)O)O

Technology Process of (3S,4S,5S,6S)-Hexahydro-1H-azepine-3,4,5,6-tetrol

There total 27 articles about (3S,4S,5S,6S)-Hexahydro-1H-azepine-3,4,5,6-tetrol 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: 100.0%

N-benzyl-3,4-di-O-benzyl-1,6-dideoxy-1,6-imino-L-iditol (157363-87-6) → 1,6-dideoxy-1,6-imino-(2S,3R,4R,5S)-L-iditol (16647-61-3,280745-41-7)

Guidance literature:

With hydrogen; palladium; In acetic acid; for 15h;

DOI:10.1016/S0040-4039(00)76888-2

Reference yield: 92.0%

(3S,4R,5R,6S)-N-diphenylmethyl-3,4,5,6-tetrahydroxyazepane (676259-81-7,280745-40-6) → 1,6-dideoxy-1,6-imino-(2S,3R,4R,5S)-L-iditol (16647-61-3,280745-41-7)

Guidance literature:

With hydrogen; palladium dihydroxide; In methanol; for 14h;

DOI:10.1016/j.bmc.2003.10.003

Reference yield: 80.0%

(3S,4R,5R,6S)-N-allyl-4,5-di-O-allyl-3,4,5,6-tetrahydroxyazepane (178909-10-9) → 1,6-dideoxy-1,6-imino-(2S,3R,4R,5S)-L-iditol (16647-61-3,280745-41-7)

Guidance literature:

With perchloric acid; palladium on activated charcoal; In methanol; for 8h; Heating;

DOI:10.1016/S0968-0896(96)00218-0

upstream raw materials:

(3S,4R,5R,6S)-1-Benzyl-4,5,6-tris-benzyloxy-azepan-3-ol

N-benzyl-3,4-di-O-benzyl-1,6-dideoxy-1,6-imino-L-iditol

(3S,4R,5R,6S)-N-allyl-4,5-di-O-allyl-3,4,5,6-tetrahydroxyazepane

(3S,4R,5R,6S)-3,4,5,6-tetrahydroxy-4,5-O-isopropylidene azepane