(1S,2S,3R,5S)-pinanediol N-BOC-L-phenylalanine-L-leucine boronate

Base Information

• Chemical Name: (1S,2S,3R,5S)-pinanediol N-BOC-L-phenylalanine-L-leucine boronate
• CAS No.: 1187479-72-6
• Molecular Formula: C₂₉H₄₅BN₂O₅
• Molecular Weight: 512.498
• Mol file: 1187479-72-6.mol

Synonyms:(1S,2S,3R,5S)-pinanediol N-BOC-L-phenylalanine-L-leucine boronate

Chemical Property of (1S,2S,3R,5S)-pinanediol N-BOC-L-phenylalanine-L-leucine boronate

Chemical Property:

Purity/Quality:

≥95% ^*data from raw suppliers

N-[(1S)-2-[[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3-methylbutyl]amino]-2-oxo-1-(phenylmethyl)ethyl]-CarbamicAcid1,1-DimethylethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: N-[(1S)-2-[[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3-methylbutyl]amino]-2-oxo-1-(phenylmethyl)ethyl]-Carbamic Acid 1,1-Dimethylethyl Ester is an intermediate in the synthesis of bortezomib (B675700).Bortezomib is the first proteasome inhibitor to be approved by the US FDA for multiple myeloma, a blood cancer.

Technology Process of (1S,2S,3R,5S)-pinanediol N-BOC-L-phenylalanine-L-leucine boronate

There total 9 articles about (1S,2S,3R,5S)-pinanediol N-BOC-L-phenylalanine-L-leucine boronate 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: 93.3%

(1R)-3-methyl-1-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxaborole-2-yl]butan-1-amine trifluoroacetatic acid salt (1310383-72-2,179324-87-9) + N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) → (1S,2S,3R,5S)-pinanediol N-BOC-L-phenylalanine-L-leucine boronate (1187479-72-6)

Guidance literature:

With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-isopropylethylamine; In acetonitrile; at -10 - 5 ℃; for 2h;

Reference yield:

(aR,3aS,4S,6S,7aR)-hexahydro-3a,8,8-trimethyl-α-(2-methylpropyl)-4,6-methano-1,3,2-benzodioxaborole-2-methanamine 2,2,2-trifluoroacetate (1310383-72-2,179324-87-9) + N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) → (1S,2S,3R,5S)-pinanediol N-BOC-L-phenylalanine-L-leucine boronate (1187479-72-6)

Guidance literature:

N-tert-butoxycarbonyl-L-phenylalanine; With benzotriazol-1-ol; In dichloromethane; at -10 ℃; for 0.166667h;

(aR,3aS,4S,6S,7aR)-hexahydro-3a,8,8-trimethyl-α-(2-methylpropyl)-4,6-methano-1,3,2-benzodioxaborole-2-methanamine 2,2,2-trifluoroacetate; With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -10 - 20 ℃; for 16h;

DOI:10.1016/j.bmc.2018.06.020

Reference yield:

(aR,3aS,4S,6S,7aR)-hexahydro-3a,8,8-trimethyl-α-(2-methylpropyl)-4,6-methano-1,3,2-benzodioxaborole-2-methanamine 2,2,2-trifluoroacetate (1310383-72-2,179324-87-9) + (1S)-(S)-pinanediol 1-ammonium trifluoroacetate-3-methylbutane-1-boronate (477254-69-6,1310383-72-2,179324-87-9) + N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) → (1S,2S,3R,5S)-pinanediol N-BOC-L-phenylalanine-L-leucine boronate (1187479-72-6) + (1S,2S,3R,5S)-pinanediol N-BOC-L-phenylalanine-L-leucine boronate

Guidance literature:

With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0.7 - 2.5 ℃; for 2.53333h; Industry scale;

upstream raw materials:

(aR,3aS,4S,6S,7aR)-hexahydro-3a,8,8-trimethyl-α-(2-methylpropyl)-4,6-methano-1,3,2-benzodioxaborole-2-methanamine 2,2,2-trifluoroacetate

(1S)-(S)-pinanediol 1-ammonium trifluoroacetate-3-methylbutane-1-boronate

N-tert-butoxycarbonyl-L-phenylalanine

(1R)-3-methyl-1-[(1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0^2,6]decan-4-yl]butan-1-amine

Downstream raw materials:

2-amino-N-((R)-3-methyl-1-((3aS,4S,6R,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)butyl)-3-phenylpropanamide hydrochloride

N-[(1S)-1[[[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3-methylbutyl]amino]carbonyl]-2-benzyl]2-pyrazine carboxamide

N-{(1S)-3-methyl-1-[(3aS,4S,6S,7aS)-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxaborol-2-yl]butyl}phenylalanine amide