(4R,5S)-4-<<(benzyloxy)carbonyl>amino>-5-methyl-3-oxoheptanoic acid, (1S,2S,3R)-4-<(tert-butyldimethylsilyl)oxy>-1-isopropyl-2-(methoxymethoxy)-3-methylbutyl ester

Base Information

• Chemical Name: (4R,5S)-4-<<(benzyloxy)carbonyl>amino>-5-methyl-3-oxoheptanoic acid, (1S,2S,3R)-4-<(tert-butyldimethylsilyl)oxy>-1-isopropyl-2-(methoxymethoxy)-3-methylbutyl ester
• CAS No.: 126587-55-1
• Molecular Formula: C₃₂H₅₅NO₈Si
• Molecular Weight: 609.876
• Mol file: 126587-55-1.mol

Synonyms:(4R,5S)-4-<<(benzyloxy)carbonyl>amino>-5-methyl-3-oxoheptanoic acid, (1S,2S,3R)-4-<(tert-butyldimethylsilyl)oxy>-1-isopropyl-2-(methoxymethoxy)-3-methylbutyl ester

Chemical Property of (4R,5S)-4-<<(benzyloxy)carbonyl>amino>-5-methyl-3-oxoheptanoic acid, (1S,2S,3R)-4-<(tert-butyldimethylsilyl)oxy>-1-isopropyl-2-(methoxymethoxy)-3-methylbutyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,5S)-4-<<(benzyloxy)carbonyl>amino>-5-methyl-3-oxoheptanoic acid, (1S,2S,3R)-4-<(tert-butyldimethylsilyl)oxy>-1-isopropyl-2-(methoxymethoxy)-3-methylbutyl ester

There total 16 articles about (4R,5S)-4-<<(benzyloxy)carbonyl>amino>-5-methyl-3-oxoheptanoic acid, (1S,2S,3R)-4-<(tert-butyldimethylsilyl)oxy>-1-isopropyl-2-(methoxymethoxy)-3-methylbutyl ester 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:

N-benzyloxycarbonylamino-D-alloisoleucine (3160-59-6,4276-05-5,28862-89-7,55723-45-0,55723-48-3,127866-12-0) → (4R,5S)-4-<<(benzyloxy)carbonyl>amino>-5-methyl-3-oxoheptanoic acid, (1S,2S,3R)-4-<(tert-butyldimethylsilyl)oxy>-1-isopropyl-2-(methoxymethoxy)-3-methylbutyl ester (126587-55-1)

Guidance literature:

Multi-step reaction with 2 steps

2: 1.) LDA / THF

With lithium diisopropyl amide;

DOI:10.1016/S0040-4039(01)80647-X

Reference yield:

methyl (S)-2-hydroxy-3-methylbutanoate (24347-63-5) → (4R,5S)-4-<<(benzyloxy)carbonyl>amino>-5-methyl-3-oxoheptanoic acid, (1S,2S,3R)-4-<(tert-butyldimethylsilyl)oxy>-1-isopropyl-2-(methoxymethoxy)-3-methylbutyl ester (126587-55-1)

Guidance literature:

Multi-step reaction with 10 steps

1: 80 percent / TfOH

2: 89 percent / LAH

3: 70 percent / SO₃*pyridine, DMSO, Et₃N

4: 74 percent / SnCl₄ / CH₂Cl₂ / -78 °C

5: LAH

6: 100 percent / DMAP, Et₃N

7: 96 percent / iPr₂NEt

8: 82 percent / Na, NH₃ / tetrahydrofuran

9: 90 percent / DMAP / CH₂Cl₂

10: 1.) LDA / THF

With dmap; lithium aluminium tetrahydride; pyridine-SO₃ complex; trifluorormethanesulfonic acid; ammonia; sodium; tin(IV) chloride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4039(01)80647-X

Reference yield:

(S)-2-Hydroxy-3-methylbutanoic acid (17407-55-5) → (4R,5S)-4-<<(benzyloxy)carbonyl>amino>-5-methyl-3-oxoheptanoic acid, (1S,2S,3R)-4-<(tert-butyldimethylsilyl)oxy>-1-isopropyl-2-(methoxymethoxy)-3-methylbutyl ester (126587-55-1)

Guidance literature:

Multi-step reaction with 11 steps

1: 87 percent / H₂SO₄

2: 80 percent / TfOH

3: 89 percent / LAH

4: 70 percent / SO₃*pyridine, DMSO, Et₃N

5: 74 percent / SnCl₄ / CH₂Cl₂ / -78 °C

6: LAH

7: 100 percent / DMAP, Et₃N

8: 96 percent / iPr₂NEt

9: 82 percent / Na, NH₃ / tetrahydrofuran

10: 90 percent / DMAP / CH₂Cl₂

11: 1.) LDA / THF

With dmap; lithium aluminium tetrahydride; pyridine-SO₃ complex; trifluorormethanesulfonic acid; ammonia; sodium; tin(IV) chloride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; sulfuric acid; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4039(01)80647-X

upstream raw materials:

N-benzyloxycarbonylamino-D-alloisoleucine

(3S,4S,5R)-6-[(tert-butyldimethylsilyl)oxy]-4-(methoxymethoxy)-2,5-dimethyl-3-hexanol acetate

[(1R,2S)-1-(Imidazole-1-carbonyl)-2-methyl-butyl]-carbamic acid benzyl ester

L-valine

Downstream raw materials:

(4R,5S)-4-<<(benzyloxy)carbonyl>amino>-3-hydroxy-5-methyl-heptanoic acid, (1S,2S,3R)-4-<(tert-butyldimethylsilyl)oxy>-1-isopropyl-2-(methoxymethoxy)-3-methylbutyl ester

(3S,4R,5S)-4-<<(benzyloxy)carbonyl>amino>-3-<(triisopropylsilyl)oxy>-5-methyl-heptanoic acid, (1S,2S,3R)-4-<(tert-butyldimethylsilyl)oxy>-1-isopropyl-2-(methoxymethoxy)-3-methylbutyl ester

(3R,4R,5S)-4-<<(benzyloxy)carbonyl>amino>-3-<(triisopropylsilyl)oxy>-5-methyl-heptanoic acid, (1S,2S,3R)-4-<(tert-butyldimethylsilyl)oxy>-1-isopropyl-2-(methoxymethoxy)-3-methylbutyl ester

N-<1--L-leucyl>-L-prolyl>-3-(p-methoxyphenyl)-N-methyl-L-alanine, ester with (3S,4R,5S)-3-<(triisopropylsilyl)oxy>-4-<(2S,3R)-2-<(tert-butoxycarbonyl)amino>-3-hydroxybutyramido>-5-methylheptanoic acid, (1S,2S,3R)-4-