(2R,4S,5S)-1-(benzyloxy)-5-<(tert-butyloxycarbonyl)amino>-4-hydroxy-2,7-dimethyloctane

Base Information

• Chemical Name: (2R,4S,5S)-1-(benzyloxy)-5-<(tert-butyloxycarbonyl)amino>-4-hydroxy-2,7-dimethyloctane
• CAS No.: 89028-19-3
• Molecular Formula: C₂₂H₃₇NO₄
• Molecular Weight: 379.54
• Mol file: 89028-19-3.mol

Synonyms:(2R,4S,5S)-1-(benzyloxy)-5-<(tert-butyloxycarbonyl)amino>-4-hydroxy-2,7-dimethyloctane

Chemical Property of (2R,4S,5S)-1-(benzyloxy)-5-<(tert-butyloxycarbonyl)amino>-4-hydroxy-2,7-dimethyloctane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4S,5S)-1-(benzyloxy)-5-<(tert-butyloxycarbonyl)amino>-4-hydroxy-2,7-dimethyloctane

There total 4 articles about (2R,4S,5S)-1-(benzyloxy)-5-<(tert-butyloxycarbonyl)amino>-4-hydroxy-2,7-dimethyloctane 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:

(R)-3-(benzyloxy)-2-methylpropan-1-ol (63930-49-4) → (2R,4S,5S)-1-(benzyloxy)-5-<(tert-butyloxycarbonyl)amino>-4-hydroxy-2,7-dimethyloctane (89028-19-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 78 percent / PPh₃, NBS / CH₂Cl₂ / 15 h / Ambient temperature

2: 1.) Mg, I₂ / 1.) THF, 12 h, 2.) THF, RT, 3.5 h

With N-Bromosuccinimide; iodine; magnesium; triphenylphosphine; In dichloromethane;

Reference yield:

benzyl bromomethyl ether (17690-16-3) → (2R,4S,5S)-1-(benzyloxy)-5-<(tert-butyloxycarbonyl)amino>-4-hydroxy-2,7-dimethyloctane (89028-19-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) LiN(Me₃Si)2 / 1.) THF, -78 deg C, 0.5 h, 2.) THF, from -78 deg C to 0 deg C, 5.5 h

2: 85 percent / Ca(BH₄)2 / ethanol; tetrahydrofuran / 0 °C

3: 78 percent / PPh₃, NBS / CH₂Cl₂ / 15 h / Ambient temperature

4: 1.) Mg, I₂ / 1.) THF, 12 h, 2.) THF, RT, 3.5 h

With N-Bromosuccinimide; calcium borohydride; iodine; magnesium; triphenylphosphine; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol; dichloromethane;

Reference yield:

(4S,5S)-3-<3-(benzyloxy)-2-methylpropionyl>-4-methyl-5-phenyl-1-oxazolidinone (80697-96-7,105943-88-2) → (2R,4S,5S)-1-(benzyloxy)-5-<(tert-butyloxycarbonyl)amino>-4-hydroxy-2,7-dimethyloctane (89028-19-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / Ca(BH₄)2 / ethanol; tetrahydrofuran / 0 °C

2: 78 percent / PPh₃, NBS / CH₂Cl₂ / 15 h / Ambient temperature

3: 1.) Mg, I₂ / 1.) THF, 12 h, 2.) THF, RT, 3.5 h

With N-Bromosuccinimide; calcium borohydride; iodine; magnesium; triphenylphosphine; In tetrahydrofuran; ethanol; dichloromethane;

upstream raw materials:

(S)-(+)-3-benzyloxy-2-methylpropyl bromide

tert-butoxycarbonyl-L-leucinal

(R)-3-(benzyloxy)-2-methylpropan-1-ol

benzyl bromomethyl ether

Downstream raw materials:

Acetic acid (S)-1-((R)-3-benzyloxy-2-methyl-propyl)-2-tert-butoxycarbonylamino-4-methyl-pentyl ester

N-<(tert-butoxycarbonyl)-L-valyl>-(2R,4R,5S)-5-amino-1-(benzyloxy)-2,7-dimethyloctan-4-ol

N-<(tert-butoxycarbonyl)-L-valyl>-(2R,4S,5S)-5-amino-1-(benzyloxy)-2,7-dimethyloctan-4-ol

Acetic acid (1S,2S)-1-((R)-3-benzyloxy-2-methyl-propyl)-2-tert-butoxycarbonylamino-4-methyl-pentyl ester