(-)-(1S,2R,4S,6R)-2,4-bis(benzyloxy)-(N-benzyloxycarbonyl)-(N-methyl)-6-aminocyclohexanol

Base Information

• Chemical Name: (-)-(1S,2R,4S,6R)-2,4-bis(benzyloxy)-(N-benzyloxycarbonyl)-(N-methyl)-6-aminocyclohexanol
• CAS No.: 218915-55-0
• Molecular Formula: C₂₉H₃₃NO₅
• Molecular Weight: 475.585
• Mol file: 218915-55-0.mol

Synonyms:(-)-(1S,2R,4S,6R)-2,4-bis(benzyloxy)-(N-benzyloxycarbonyl)-(N-methyl)-6-aminocyclohexanol

Chemical Property of (-)-(1S,2R,4S,6R)-2,4-bis(benzyloxy)-(N-benzyloxycarbonyl)-(N-methyl)-6-aminocyclohexanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(1S,2R,4S,6R)-2,4-bis(benzyloxy)-(N-benzyloxycarbonyl)-(N-methyl)-6-aminocyclohexanol

There total 1 articles about (-)-(1S,2R,4S,6R)-2,4-bis(benzyloxy)-(N-benzyloxycarbonyl)-(N-methyl)-6-aminocyclohexanol 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: 78.0%

benzyl chloroformate (501-53-1,94274-21-2) + (1S,2R,4S,6R)-2,4-Bis-benzyloxy-6-methylamino-cyclohexanol (218915-51-6) → (-)-(1S,2R,4S,6R)-2,4-bis(benzyloxy)-(N-benzyloxycarbonyl)-(N-methyl)-6-aminocyclohexanol (218915-55-0)

Guidance literature:

With dmap; TEA; In dichloromethane; at 20 ℃; for 16h;

DOI:10.1039/b312808c

Reference yield:

methylphosphonic acid dichloroanhydride (676-97-1) + (-)-(1S,2R,4S,6R)-2,4-bis(benzyloxy)-(N-benzyloxycarbonyl)-(N-methyl)-6-aminocyclohexanol (218915-55-0) → C30H35ClNO6P

Guidance literature:

With dmap; TEA; In dichloromethane; at 20 ℃; for 16h;

DOI:10.1039/b312808c

Reference yield:

(-)-(1S,2R,4S,6R)-2,4-bis(benzyloxy)-(N-benzyloxycarbonyl)-(N-methyl)-6-aminocyclohexanol (218915-55-0) → 6-methylamino-1,2,4-trihydroxycyclohexane 1-phosphate (218915-60-7)

Guidance literature:

Multi-step reaction with 3 steps

1: TEA, DMAP / CH₂Cl₂ / 12 h / 20 °C

2: tetrahydrofuran / 2 h / -70 °C

3: H₂ / Pd/C / methanol / 24 h

With dmap; TEA; hydrogen; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/S0040-4039(98)01909-1

upstream raw materials:

benzyl chloroformate

(1S,2R,4S,6R)-2,4-Bis-benzyloxy-6-methylamino-cyclohexanol

Downstream raw materials:

6-methylamino-1,2,4-trihydroxycyclohexane 1-phosphate

[(1R,2S,3R,5S)-3,5-Bis-benzyloxy-2-(bis-benzyloxy-phosphoryloxy)-cyclohexyl]-methyl-carbamic acid benzyl ester