(4R,9R)-9-Allyloxycarbonylamino-4-(3-benzyloxy-propyl)-10-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-6-(toluene-4-sulfonyl)-decanoic acid methyl ester

Base Information

• Chemical Name: (4R,9R)-9-Allyloxycarbonylamino-4-(3-benzyloxy-propyl)-10-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-6-(toluene-4-sulfonyl)-decanoic acid methyl ester
• CAS No.: 253882-53-0
• Molecular Formula: C₃₈H₅₉NO₉SSi
• Molecular Weight: 734.039
• Mol file: 253882-53-0.mol

Synonyms:(4R,9R)-9-Allyloxycarbonylamino-4-(3-benzyloxy-propyl)-10-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-6-(toluene-4-sulfonyl)-decanoic acid methyl ester

Chemical Property of (4R,9R)-9-Allyloxycarbonylamino-4-(3-benzyloxy-propyl)-10-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-6-(toluene-4-sulfonyl)-decanoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,9R)-9-Allyloxycarbonylamino-4-(3-benzyloxy-propyl)-10-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-6-(toluene-4-sulfonyl)-decanoic acid methyl ester

There total 9 articles about (4R,9R)-9-Allyloxycarbonylamino-4-(3-benzyloxy-propyl)-10-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-6-(toluene-4-sulfonyl)-decanoic acid methyl 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: 77.0%

(R)-7-Benzyloxy-4-formyl-heptanoic acid methyl ester (253882-52-9) + [1-(tert-butyl-dimethyl-silanyloxymethyl)-4-(toluene-4-sulfonyl)-butyl]-carbamic acid allyl ester (253882-46-1) → (4R,9R)-9-Allyloxycarbonylamino-4-(3-benzyloxy-propyl)-10-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-6-(toluene-4-sulfonyl)-decanoic acid methyl ester (253882-53-0)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.75h;

DOI:10.1016/S0040-4039(99)01815-8

Reference yield:

di(p-tolyl) disulfide (103-19-5) → (4R,9R)-9-Allyloxycarbonylamino-4-(3-benzyloxy-propyl)-10-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-6-(toluene-4-sulfonyl)-decanoic acid methyl ester (253882-53-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 85 percent / Bu₃P / CH₂Cl₂ / 3 h

2: 91 percent / OsO₄; N-methylmorpholine N-oxide / tetrahydrofuran; H₂O; acetone / 8 h

3: CF₃COOH; Me₂S / CH₂Cl₂ / 3 h

4: pyridine / 0.5 h / 0 °C

5: NaBH₄; CaCl₂ / tetrahydrofuran; ethanol

6: imdazole / tetrahydrofuran / 3 h

7: 77 percent / BuLi / tetrahydrofuran / 0.75 h / -78 °C

With pyridine; 1H-imidazole; sodium tetrahydroborate; osmium(VIII) oxide; n-butyllithium; dimethylsulfide; tributylphosphine; 4-methylmorpholine N-oxide; trifluoroacetic acid; calcium chloride; In tetrahydrofuran; ethanol; dichloromethane; water; acetone; 1: Substitution / 2: Oxidation / 3: Hydrolysis / 4: Acylation / 5: Reduction / 6: Etherification / 7: Addition;

DOI:10.1016/S0040-4039(99)01815-8

Reference yield:

(R)-2-Amino-5-(toluene-4-sulfonyl)-pentanoic acid methyl ester (253882-43-8) → (4R,9R)-9-Allyloxycarbonylamino-4-(3-benzyloxy-propyl)-10-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-6-(toluene-4-sulfonyl)-decanoic acid methyl ester (253882-53-0)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine / 0.5 h / 0 °C

2: NaBH₄; CaCl₂ / tetrahydrofuran; ethanol

3: imdazole / tetrahydrofuran / 3 h

4: 77 percent / BuLi / tetrahydrofuran / 0.75 h / -78 °C

With pyridine; 1H-imidazole; sodium tetrahydroborate; n-butyllithium; calcium chloride; In tetrahydrofuran; ethanol; 1: Acylation / 2: Reduction / 3: Etherification / 4: Addition;

DOI:10.1016/S0040-4039(99)01815-8

upstream raw materials:

(R)-7-Benzyloxy-4-formyl-heptanoic acid methyl ester

[1-(tert-butyl-dimethyl-silanyloxymethyl)-4-(toluene-4-sulfonyl)-butyl]-carbamic acid allyl ester

di(p-tolyl) disulfide

(R)-2-Amino-5-(toluene-4-sulfonyl)-pentanoic acid methyl ester

Downstream raw materials:

(4R,9R)-9-Allyloxycarbonylamino-4-(3-benzyloxy-propyl)-10-(tert-butyl-dimethyl-silanyloxy)-5-oxo-6-(toluene-4-sulfonyl)-decanoic acid methyl ester

(R)-7-Benzyloxy-4-[(R)-6-(tert-butyl-dimethyl-silanyloxymethyl)-3-(toluene-4-sulfonyl)-1,4,5,6-tetrahydro-pyridin-2-yl]-heptanoic acid methyl ester

(1R,6R)-1-(3-Benzyloxy-propyl)-6-(tert-butyl-dimethyl-silanyloxymethyl)-9-(toluene-4-sulfonyl)-1,2,3,6,7,8-hexahydro-quinolizin-4-one

(R)-4-[(R)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-3-(toluene-4-sulfonyl)-1,4,5,6-tetrahydro-pyridin-2-yl]-7-hydroxy-heptanoic acid methyl ester