(2R,3S)-methyl 2-((2S,3R)-3-benzyl-2-(benzyloxycarbonylamino)-4-(tert-butyldiphenylsilyloxy)butanamido)-3-hydroxybutanoate

Base Information

• Chemical Name: (2R,3S)-methyl 2-((2S,3R)-3-benzyl-2-(benzyloxycarbonylamino)-4-(tert-butyldiphenylsilyloxy)butanamido)-3-hydroxybutanoate
• CAS No.: 892397-08-9
• Molecular Formula: C₄₀H₄₈N₂O₇Si
• Molecular Weight: 696.916
• Mol file: 892397-08-9.mol

Synonyms:(2R,3S)-methyl 2-((2S,3R)-3-benzyl-2-(benzyloxycarbonylamino)-4-(tert-butyldiphenylsilyloxy)butanamido)-3-hydroxybutanoate

Chemical Property of (2R,3S)-methyl 2-((2S,3R)-3-benzyl-2-(benzyloxycarbonylamino)-4-(tert-butyldiphenylsilyloxy)butanamido)-3-hydroxybutanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-methyl 2-((2S,3R)-3-benzyl-2-(benzyloxycarbonylamino)-4-(tert-butyldiphenylsilyloxy)butanamido)-3-hydroxybutanoate

There total 6 articles about (2R,3S)-methyl 2-((2S,3R)-3-benzyl-2-(benzyloxycarbonylamino)-4-(tert-butyldiphenylsilyloxy)butanamido)-3-hydroxybutanoate 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: 100.0%

(5S,6R)-6-benzyl-10,10-dimethyl-3-oxo-1,9,9-triphenyl-2,8-dioxa-4-aza-9-silaundecane-5-carboxylic acid (892397-07-8) + (2R,3S)-2-amino-3-hydroxy-butyric acid methyl ester hydrochloride (60538-15-0) → (2R,3S)-methyl 2-((2S,3R)-3-benzyl-2-(benzyloxycarbonylamino)-4-(tert-butyldiphenylsilyloxy)butanamido)-3-hydroxybutanoate (892397-08-9)

Guidance literature:

(5S,6R)-6-benzyl-10,10-dimethyl-3-oxo-1,9,9-triphenyl-2,8-dioxa-4-aza-9-silaundecane-5-carboxylic acid; With 4-methyl-morpholine; isobutyl chloroformate; In dichloromethane; at -20 ℃; for 0.0833333h;

(2R,3S)-2-amino-3-hydroxy-butyric acid methyl ester hydrochloride; With triethylamine; In dichloromethane; N,N-dimethyl-formamide; at -20 - 20 ℃;

DOI:10.1021/ol060677c

Reference yield:

(2S,3R)-methyl 2-amino-3-benzyl-4-(tert-butyldiphenylsilyloxy)butanoate (892397-17-0) → (2R,3S)-methyl 2-((2S,3R)-3-benzyl-2-(benzyloxycarbonylamino)-4-(tert-butyldiphenylsilyloxy)butanamido)-3-hydroxybutanoate (892397-08-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 91 percent / NaHCO₃ / ethyl acetate; H₂O / 14 h / 20 °C

2.1: 96 percent / LiOH*H₂O / tetrahydrofuran; H₂O / 36 h / 20 °C

3.1: isobutyl chloroformate; N-methylmorpholine / CH₂Cl₂ / 0.08 h / -20 °C

3.2: 100 percent / Et₃N / CH₂Cl₂; dimethylformamide / -20 - 20 °C

With 4-methyl-morpholine; lithium hydroxide; sodium hydrogencarbonate; isobutyl chloroformate; In tetrahydrofuran; dichloromethane; water; ethyl acetate;

DOI:10.1021/ol060677c

Reference yield:

(6R,7S)-methyl 6-benzyl-2,2,11,11-tetramethyl-9-oxo-3,3-diphenyl-4,10-dioxa-8-aza-3-siladodecane-7-carboxylate (892397-16-9) → (2R,3S)-methyl 2-((2S,3R)-3-benzyl-2-(benzyloxycarbonylamino)-4-(tert-butyldiphenylsilyloxy)butanamido)-3-hydroxybutanoate (892397-08-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 99 percent / trifluoroacetic acid; thioanisole / CH₂Cl₂ / 0.67 h / 17 °C

2.1: 91 percent / NaHCO₃ / ethyl acetate; H₂O / 14 h / 20 °C

3.1: 96 percent / LiOH*H₂O / tetrahydrofuran; H₂O / 36 h / 20 °C

4.1: isobutyl chloroformate; N-methylmorpholine / CH₂Cl₂ / 0.08 h / -20 °C

4.2: 100 percent / Et₃N / CH₂Cl₂; dimethylformamide / -20 - 20 °C

With 4-methyl-morpholine; lithium hydroxide; methyl-phenyl-thioether; sodium hydrogencarbonate; trifluoroacetic acid; isobutyl chloroformate; In tetrahydrofuran; dichloromethane; water; ethyl acetate;

DOI:10.1021/ol060677c

upstream raw materials:

(5S,6R)-6-benzyl-10,10-dimethyl-3-oxo-1,9,9-triphenyl-2,8-dioxa-4-aza-9-silaundecane-5-carboxylic acid

(2R,3S)-2-amino-3-hydroxy-butyric acid methyl ester hydrochloride

(2S,3R)-methyl 2-amino-3-benzyl-4-(tert-butyldiphenylsilyloxy)butanoate

(6R,7S)-methyl 6-benzyl-2,2,11,11-tetramethyl-9-oxo-3,3-diphenyl-4,10-dioxa-8-aza-3-siladodecane-7-carboxylate

Downstream raw materials:

(4R,5R)-methyl 2-((5S,6R)-6-benzyl-10,10-dimethyl-3-oxo-1,9,9-triphenyl-2,8-dioxa-4-aza-9-silaundecan-5-yl)-5-methyl-4,5-dihydrooxazole-4-carboxylate

cyclo[γ-phenyl-allo-homoThr(TBDPS)-D-Thr(oxaz)-Val-D-Thr(oxaz)-Val-D-Thr(oxaz)]

cyclo[γ-phenyl-allo-homoThr-D-Thr(oxaz)-Val-D-Thr(oxaz)-Val-D-Thr(oxaz)] pent-4-enoate

cyclo[γ-phenyl-allo-homoThr-D-Thr(oxaz)-Val-D-Thr(oxaz)-Val-D-Thr(oxaz)]