Boc-(2R,3S)-3-amino-2-hydroxy-5-methylhexanoic acid

Base Information

• Chemical Name: Boc-(2R,3S)-3-amino-2-hydroxy-5-methylhexanoic acid
• CAS No.: 73397-28-1
• Molecular Formula: C₁₂H₂₃NO₅
• Molecular Weight: 261.318
• Hs Code.: 2924297099
• European Community (EC) Number: 689-930-1
• Nikkaji Number: J863.601J
• Mol file: 73397-28-1.mol

Synonyms:73397-28-1;Boc-(2R,3S)-3-amino-2-hydroxy-5-methylhexanoic acid;(2R,3S)-3-((tert-Butoxycarbonyl)amino)-2-hydroxy-5-methylhexanoic acid;(2R,3S)-2-hydroxy-5-methyl-3-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoic acid;(2R,3S)-3-(Boc-amino)-2-hydroxy-5-methylhexanoic acid;Boc-(2R,3S)-3-amino-2-hydroxy-5-methylhexanoicacid;SCHEMBL3446599;N-BOC-(2R,3S)-2-HYDROXY-3-AMINO-5-METHYLHEXANOIC ACID;YCA39728;MFCD04972275;AKOS027327496;CS-0331192;(2R,3S)-3-(tert-butoxycarbonylamino)-2-hydroxy-5-methyl-hexanoic acid;(2R,3S)-3-(tert-butoxycarbonylamino)-2-hydroxy-5-methylhexanoic acid;(2R,3S)-3-{[(tert-butoxy)carbonyl]amino}-2-hydroxy-5-methylhexanoic acid

Chemical Property of Boc-(2R,3S)-3-amino-2-hydroxy-5-methylhexanoic acid

Chemical Property:

• Boiling Point: 419.7±35.0 °C(Predicted)
• PKA: 3?+-.0.34(Predicted)
• PSA: 95.86000
• Density: 1.125±0.06 g/cm3(Predicted)
• LogP: 1.76220
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 261.15762283
• Heavy Atom Count: 18
• Complexity: 295

Purity/Quality:

99% ^*data from raw suppliers

N-Boc-(2R,3S)-2-hydroxy-3-amino-5-methylhexanoicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CC(C(C(=O)O)O)NC(=O)OC(C)(C)C
• Isomeric SMILES: CC(C)C[C@@H]([C@H](C(=O)O)O)NC(=O)OC(C)(C)C

Technology Process of Boc-(2R,3S)-3-amino-2-hydroxy-5-methylhexanoic acid

There total 6 articles about Boc-(2R,3S)-3-amino-2-hydroxy-5-methylhexanoic 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: 73.0%

N-(tert-butyloxycarbonyl) azide (1070-19-5) + (2RS,3R)-3-Amino-2-hydroxy-5-methylhexanoic Acid (62023-30-7,70853-11-1,70853-17-7,73397-20-3,73397-21-4,75556-30-8) → (2RS,3R)-3-<<(tert-Butyloxy)carbonyl>amino>-2-hydroxy-5-methylhexanoic Acid (73397-25-8,73397-26-9,73397-27-0,73397-28-1,77119-88-1)

Guidance literature:

With triethylamine; In 1,4-dioxane; water; at 25 ℃;

DOI:10.1021/jo01300a004

Reference yield:

(R)-4-methyl-1-oxopentane-2-benzylcarbamate (70853-26-8) → (2RS,3R)-3-<<(tert-Butyloxy)carbonyl>amino>-2-hydroxy-5-methylhexanoic Acid (73397-25-8,73397-26-9,73397-27-0,73397-28-1,77119-88-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) NaHSO₃ / 1.) 5 deg C, overnight, 2.) ethyl acetate, water, room temp., 4 h

2: 90 percent / concentrated HCl / dioxane / 12 h / Heating

3: 73 percent / triethylamine / H₂O; dioxane / 25 °C

With hydrogenchloride; sodium hydrogensulfite; triethylamine; In 1,4-dioxane; water;

DOI:10.1021/jo01300a004

Reference yield:

[(S)-1-((S)-Cyano-hydroxy-methyl)-3-methyl-butyl]-carbamic acid benzyl ester (63219-62-5,73397-23-6,73397-24-7,106868-70-6,106868-79-5) → (2RS,3R)-3-<<(tert-Butyloxy)carbonyl>amino>-2-hydroxy-5-methylhexanoic Acid (73397-25-8,73397-26-9,73397-27-0,73397-28-1,77119-88-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / concentrated HCl / dioxane / 12 h / Heating

2: 73 percent / triethylamine / H₂O; dioxane / 25 °C

With hydrogenchloride; triethylamine; In 1,4-dioxane; water;

DOI:10.1021/jo01300a004

upstream raw materials:

N-(tert-butyloxycarbonyl) azide

DL-threo-3-amino-2-hydroxy-5-methylhexanoic acid

(2RS,3R)-3-Amino-2-hydroxy-5-methylhexanoic Acid

(R)-4-methyl-1-oxopentane-2-benzylcarbamate

Downstream raw materials:

(2R,3S)-3-amino-2-hydroxy-5-methylhexanoic acid

(2S,3S)-3-Amino-2-hydroxy-5-methylhexanoic Acid

(2S,3S)-3-[(tert-butoxycarbonyl)amino]-2-hydroxy-5-methylhexanoic acid

(2S,3R)-3-<<(tert-Butyloxy)carbonyl>amino>-2-hydroxy-5-methylhexanoic Acid

Refernces

• 1、 Rich, Daniel H.,Moon, Byung Jo,Boparai, Amrit S.. "Synthesis of (2S,3R)-3-Amino-2-hydroxy-5-methylhexanoic Acid Derivatives. Application to the Synthesis of Amastatin, an Inhibitor of Aminopeptidases". . p. 2288 - 2290. Retrieved 2007/10/02.