(3S,4aS,8aS)-2-Carbobenzyloxy-decahydro-3-isoquinolinecarboxylic Acid

Base Information

• Chemical Name: (3S,4aS,8aS)-2-Carbobenzyloxy-decahydro-3-isoquinolinecarboxylic Acid
• CAS No.: 136465-85-5
• Molecular Formula: C18H23NO4
• Molecular Weight: 317.37952
• DSSTox Substance ID: DTXSID40595369
• Wikidata: Q82490369
• Mol file: 136465-85-5.mol

Synonyms:136465-85-5;(3S,4aS,8aS)-2-Carbobenzyloxy-decahydro-3-isoquinolinecarboxylic Acid;(3S,4aS,8aS)-2-phenylmethoxycarbonyl-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinoline-3-carboxylic acid;(3S,4AS,8aS)-2-((benzyloxy)carbonyl)decahydroisoquinoline-3-carboxylic acid;(3S,4aS,8aS)-2-[(Benzyloxy)carbonyl]decahydroisoquinoline-3-carboxylic acid;SCHEMBL8951577;DTXSID40595369;(3S,4aS,8aS)-2-[(benzyloxy)carbonyl]-decahydroisoquinoline-3-carboxylic acid;DB-257695

Chemical Property of (3S,4aS,8aS)-2-Carbobenzyloxy-decahydro-3-isoquinolinecarboxylic Acid

Chemical Property:

• Boiling Point: 495.9±38.0 °C(Predicted)
• PKA: 4.02±0.20(Predicted)
• PSA: 66.84000
• Density: 1.220±0.06 g/cm3(Predicted)
• LogP: 3.22640
• Solubility.: Ethanol, Methanol
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 317.16270821
• Heavy Atom Count: 23
• Complexity: 433

Purity/Quality:

95% ^*data from raw suppliers

(3S,4aS,8aS)-2-Carbobenzyloxy-decahydro-3-isoquinolinecarboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC2CN(C(CC2C1)C(=O)O)C(=O)OCC3=CC=CC=C3
• Isomeric SMILES: C1CC[C@@H]2CN([C@@H](C[C@@H]2C1)C(=O)O)C(=O)OCC3=CC=CC=C3
• Uses: (3S,4aS,8aS)-2-Carbobenzyloxy-decahydro-3-isoquinolinecarboxylic Acid (cas# 136465-85-5) is a compound useful in organic synthesis.

Technology Process of (3S,4aS,8aS)-2-Carbobenzyloxy-decahydro-3-isoquinolinecarboxylic Acid

There total 4 articles about (3S,4aS,8aS)-2-Carbobenzyloxy-decahydro-3-isoquinolinecarboxylic Acid 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%

benzyl chloroformate (501-53-1,94274-21-2) + (3R,4aS,8aS)-Decahydro-isoquinoline-3-carboxylic acid (173325-14-9) → (3R,4aS,8aS)-Octahydro-isoquinoline-2,3-dicarboxylic acid 2-benzyl ester (169390-43-6,136465-85-5)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; for 2h; Ambient temperature; pH 9.8;

DOI:10.1021/jm00022a009

Reference yield:

(3R)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (103733-65-9) → (3R,4aS,8aS)-Octahydro-isoquinoline-2,3-dicarboxylic acid 2-benzyl ester (169390-43-6,136465-85-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / H₂, aq.HCl / 5percent Rh/Al₂O₃ / 16 h / 120 °C / 103430 Torr

2: 85 percent / aq.NaOH / tetrahydrofuran / 2 h / Ambient temperature; pH 9.8

With hydrogenchloride; sodium hydroxide; hydrogen; Rh/Al₂O₃; In tetrahydrofuran;

DOI:10.1021/jm00022a009

Reference yield:

decahydro-3-isoquinolinecarboxylic acid (82717-30-4) + rhodium-on-charcoal + benzyl chloroformate (501-53-1,94274-21-2) + N-cyclohexyl-cyclohexanamine (101-83-7) → 2-(benzyloxycarbonyl)-decahydro-(4AS,8AS)-isoquinoline-3(S)-carboxylic acid (136465-85-5)

Guidance literature:

In sodium hydroxide; di-isopropyl ether; acetic acid;

upstream raw materials:

benzyl chloroformate

(3R,4aS,8aS)-Decahydro-isoquinoline-3-carboxylic acid

(3R)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

decahydro-3-isoquinolinecarboxylic acid

Refernces

• 1、 -. "Alcohols". . . Retrieved 2008/06/13.
• 2、 -. "Bicyclic α-iminocarboxylic acid compounds having hypotensive activity". . . Retrieved 2008/06/13.