(1R,5R)-8-Azabicyclo[3.2.1]octane-1,2alpha,3alpha,4beta-tetrol

Base Information

• Chemical Name: (1R,5R)-8-Azabicyclo[3.2.1]octane-1,2alpha,3alpha,4beta-tetrol
• CAS No.: 178231-95-3
• Molecular Formula: C7H13NO4
• Molecular Weight: 175.18
• DSSTox Substance ID: DTXSID101319081
• Nikkaji Number: J657.465C
• Wikidata: Q105003868
• ChEMBL ID: CHEMBL3233944
• Mol file: 178231-95-3.mol

Synonyms:1,2,3,4-tetrahydroxy-nor-tropane;calystegine B(2);calystegine B(3);calystegine B(4);calystegine B2;calystegine B3;calystegine B4

Chemical Property of (1R,5R)-8-Azabicyclo[3.2.1]octane-1,2alpha,3alpha,4beta-tetrol

Chemical Property:

• Boiling Point: 341.0±42.0 °C(Predicted)
• PKA: 13.45±0.70(Predicted)
• PSA: 92.95000
• Density: 1.722±0.06 g/cm3(Predicted)
• LogP: -2.14790
• XLogP3: -2.4
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 0
• Exact Mass: 175.08445790
• Heavy Atom Count: 12
• Complexity: 200

Purity/Quality:

98% ^*data from raw suppliers

Calystegine B3 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1CC2(C(C(C(C1N2)O)O)O)O
• Isomeric SMILES: C1C[C@]2([C@@H]([C@@H]([C@H]([C@@H]1N2)O)O)O)O

Technology Process of (1R,5R)-8-Azabicyclo[3.2.1]octane-1,2alpha,3alpha,4beta-tetrol

There total 60 articles about (1R,5R)-8-Azabicyclo[3.2.1]octane-1,2alpha,3alpha,4beta-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: 90.0%

(2S,3R,4S,5R)-5-[N-benzyl-N-(benzyloxycarbonyl)amino]-2,3,4-tris(benzyloxy)cycloheptanone (332178-31-1) → calystegin B2 (127414-85-1,178231-95-3)

Guidance literature:

With hydrogenchloride; hydrogen; palladium dihydroxide; In tetrahydrofuran; at 20 ℃; for 48h; under 760 Torr;

DOI:10.1021/jo020645c

Reference yield: 81.0%

(2R,3R,4S,5R)-5-[N-benzyl-N-(benzyloxycarbonyl)-amine]-2,3,4-tris(benzyloxy)-cyclo-hept-6-en-1-one → calystegin B2 (127414-85-1,178231-95-3)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; acetic acid; for 48h;

DOI:10.1039/c6ob00697c

Reference yield: 60.0%

(2S,3R,4S,5R)-5-Azido-2,3,4-tris-benzyloxy-cycloheptanone (146176-81-0) → calystegin B2 (127414-85-1,178231-95-3)

Guidance literature:

With hydrogen; palladium; In acetic acid;

DOI:10.1016/S0040-4039(00)74717-4

upstream raw materials:

(2S,3R,4S,5R)-5-Azido-2,3,4-tris-benzyloxy-cycloheptanone

(2S,3R,4S,5S) 5-azido-2,3,4-tris(benzyloxy) cyclohept-6,7-en-1-one

(2S,3R,4S,5R)-2,4-dibenzyloxy-5-benzyloxycarbonylamino-3-hydroxycyclohept-6-en-1-one

(2S,3R,4S,5R)-5-[N-benzyl-N-(benzyloxycarbonyl)amino]-2,3,4-tris(benzyloxy)cycloheptanone

Refernces

• 1、 Wang, Hong-Yao,Kato, Atsushi,Kinami, Kyoko,Li, Yi-Xian,Fleet, George W. J.,Yu, Chu-Yi. "Concise synthesis of calystegines B2 and B3: Via intramolecular Nozaki-Hiyama-Kishi reaction". . p. 4885 - 4896. Retrieved 2016/06/13.
• 2、 Kamimura, Akio,Miyazaki, Koichiro,Suzuki, Shuzo,Ishikawa, Shingo,Uno, Hidemitsu. "Total synthesis of ent-calystegine B4 via nitro-Michael/aldol reaction". . p. 4362 - 4366. Retrieved 2012/06/18.