(1R,3R)-3-(((Benzyloxy)carbonyl)amino)cyclohexyl acetate

Base Information

• Chemical Name: (1R,3R)-3-(((Benzyloxy)carbonyl)amino)cyclohexyl acetate
• CAS No.: 750649-42-4
• Molecular Formula: C₁₆H₂₁NO₄
• Molecular Weight: 291.347
• DSSTox Substance ID: DTXSID701196273
• Nikkaji Number: J2.075.403F
• Mol file: 750649-42-4.mol

Synonyms:750649-42-4;(1R,3R)-3-(((Benzyloxy)carbonyl)amino)cyclohexyl acetate;Carbamic acid, [(1R,3R)-3-(acetyloxy)cyclohexyl]-, phenylmethyl ester;(1R,3R)-3-{[(benzyloxy)carbonyl]amino}cyclohexyl acetate;DTXSID701196273;MFCD30472098;AKOS030628368;AS-72571;W13051;(1R,3R)-3-(((Benzyloxy)carbonyl)amino)cyclohexylacetate;[(1R,3R)-3-(phenylmethoxycarbonylamino)cyclohexyl] acetate;Phenylmethyl N-[(1R,3R)-3-(acetyloxy)cyclohexyl]carbamate

Chemical Property of (1R,3R)-3-(((Benzyloxy)carbonyl)amino)cyclohexyl acetate

Chemical Property:

• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 291.14705815
• Heavy Atom Count: 21
• Complexity: 352

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=O)OC1CCCC(C1)NC(=O)OCC2=CC=CC=C2
• Isomeric SMILES: CC(=O)O[C@@H]1CCC[C@H](C1)NC(=O)OCC2=CC=CC=C2

Technology Process of (1R,3R)-3-(((Benzyloxy)carbonyl)amino)cyclohexyl acetate

There total 8 articles about (1R,3R)-3-(((Benzyloxy)carbonyl)amino)cyclohexyl acetate 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: 40.0%

vinyl acetate (108-05-4,9003-20-7) + (+/-)-trans-(3-hydroxycyclohexyl)carbamic acid benzyl ester (750649-39-9,750649-44-6) → ((1R,3R)-3-hydroxycyclohexyl)carbamic acid benzyl ester (750649-39-9,750649-44-6) + ((1S,3S)-3-hydroxycyclohexyl)carbamic acid benzyl ester (750649-39-9,750649-44-6) + acetic acid (1R,3R)-3-(benzyloxycarbonylamino)cyclohexyl ester (750649-42-4)

Guidance literature:

With CAL-B; In tetrahydrofuran; at 30 ℃; for 3h; Enzymatic reaction;

DOI:10.1016/j.tetasy.2004.05.035

Reference yield: 36.8%

vinyl acetate (108-05-4,9003-20-7) + (+/-)-trans-(3-hydroxycyclohexyl)carbamic acid benzyl ester (750649-39-9,750649-44-6) → ((1S,3S)-3-hydroxycyclohexyl)carbamic acid benzyl ester (750649-39-9,750649-44-6) + acetic acid (1R,3R)-3-(benzyloxycarbonylamino)cyclohexyl ester (750649-42-4)

Guidance literature:

With Candida antarctica lipase (Novozym 435); In tetrahydrofuran; at 20 ℃; for 108h; optical yield given as %ee; Enzymatic reaction;

DOI:10.1021/op1002424

Reference yield:

3-aminocyclohexanol (6850-39-1) → ((1S,3S)-3-hydroxycyclohexyl)carbamic acid benzyl ester (750649-39-9,750649-44-6) + acetic acid (1R,3R)-3-(benzyloxycarbonylamino)cyclohexyl ester (750649-42-4)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydrogencarbonate / water / 16 h / 20 °C

2: Candida antarctica lipase (Novozym 435) / tetrahydrofuran / 108 h / 20 °C / Enzymatic reaction

With sodium hydrogencarbonate; In tetrahydrofuran; water;

DOI:10.1021/op1002424

upstream raw materials:

vinyl acetate

(+/-)-trans-(3-hydroxycyclohexyl)carbamic acid benzyl ester

(+/-)-trans-3-aminocyclohexanol

(+/-)-cis-2-(3-hydroxycyclohexyl)isoindole-1,3-dione

Downstream raw materials:

5,5,6,6-tetramethyl-2-(4-nitrophenoxy)-5,6-dihydro-1,4,3-oxathiazine 4,4-dioxide

((1R,3R)-3-hydroxycyclohexyl)carbamic acid benzyl ester