(5R,6S)-7-benzyloxy-6-benzyloxycarbonylamino-5-(tert-butyl-dimethyl-silanyloxy)-3-oxoheptanoic acid methyl ester

Base Information

• Chemical Name: (5R,6S)-7-benzyloxy-6-benzyloxycarbonylamino-5-(tert-butyl-dimethyl-silanyloxy)-3-oxoheptanoic acid methyl ester
• CAS No.: 752251-12-0
• Molecular Formula: C₂₉H₄₁NO₇Si
• Molecular Weight: 543.733
• Mol file: 752251-12-0.mol

Synonyms:(5R,6S)-7-benzyloxy-6-benzyloxycarbonylamino-5-(tert-butyl-dimethyl-silanyloxy)-3-oxoheptanoic acid methyl ester

Chemical Property of (5R,6S)-7-benzyloxy-6-benzyloxycarbonylamino-5-(tert-butyl-dimethyl-silanyloxy)-3-oxoheptanoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5R,6S)-7-benzyloxy-6-benzyloxycarbonylamino-5-(tert-butyl-dimethyl-silanyloxy)-3-oxoheptanoic acid methyl ester

There total 8 articles about (5R,6S)-7-benzyloxy-6-benzyloxycarbonylamino-5-(tert-butyl-dimethyl-silanyloxy)-3-oxoheptanoic 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:

monomethyl monopotassium malonate (38330-80-2) + [(1S,2R)-1-Benzyloxymethyl-2-(tert-butyl-dimethyl-silanyloxy)-4-imidazol-1-yl-4-oxo-butyl]-carbamic acid benzyl ester → (5R,6S)-7-benzyloxy-6-benzyloxycarbonylamino-5-(tert-butyl-dimethyl-silanyloxy)-3-oxoheptanoic acid methyl ester (752251-12-0)

Guidance literature:

monomethyl monopotassium malonate; With magnesium chloride; In tetrahydrofuran; for 5h; Heating;

[(1S,2R)-1-Benzyloxymethyl-2-(tert-butyl-dimethyl-silanyloxy)-4-imidazol-1-yl-4-oxo-butyl]-carbamic acid benzyl ester; In tetrahydrofuran; at 20 ℃; for 16h;

DOI:10.1002/anie.200453909

Reference yield:

Z-Ser(Bzl)-OH (20806-43-3) → (5R,6S)-7-benzyloxy-6-benzyloxycarbonylamino-5-(tert-butyl-dimethyl-silanyloxy)-3-oxoheptanoic acid methyl ester (752251-12-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: tetrahydrofuran / 2 h / 0 - 20 °C

2.1: MgCl₂ / tetrahydrofuran / 5 h / Heating

2.2: 34.2 g / tetrahydrofuran / 16 h / 20 °C

3.1: 48 percent / NaBH₄ / methanol; diethyl ether / 6 h / -60 °C

4.1: 78 percent / 2,6-lutidine / CH₂Cl₂ / -20 - 20 °C

5.1: 54 percent / aq. NaOH / tetrahydrofuran; methanol / 4 h / 0 - 20 °C

6.1: tetrahydrofuran / 1 h / 0 °C

7.1: MgCl₂ / tetrahydrofuran / 5 h / Heating

7.2: 3.38 g / tetrahydrofuran / 16 h / 20 °C

With 2,6-dimethylpyridine; sodium hydroxide; sodium tetrahydroborate; magnesium chloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 2.2: Claisen condensation / 7.2: Claisen condensation;

DOI:10.1002/anie.200453909

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → (5R,6S)-7-benzyloxy-6-benzyloxycarbonylamino-5-(tert-butyl-dimethyl-silanyloxy)-3-oxoheptanoic acid methyl ester (752251-12-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 78 percent / 2,6-lutidine / CH₂Cl₂ / -20 - 20 °C

2.1: 54 percent / aq. NaOH / tetrahydrofuran; methanol / 4 h / 0 - 20 °C

3.1: tetrahydrofuran / 1 h / 0 °C

4.1: MgCl₂ / tetrahydrofuran / 5 h / Heating

4.2: 3.38 g / tetrahydrofuran / 16 h / 20 °C

With 2,6-dimethylpyridine; sodium hydroxide; magnesium chloride; In tetrahydrofuran; methanol; dichloromethane; 4.2: Claisen condensation;

DOI:10.1002/anie.200453909

upstream raw materials:

monomethyl monopotassium malonate

t-butyldimethylsiyl triflate

Z-Ser(Bzl)-OH

(4S)-5-benzyloxy-4-benzyloxycarbonylamino-3-oxo-pentanoic acid methyl ester

Downstream raw materials:

(3R,5R,6S)-6-(2-benzyloxybenzoylamino)-3,5,7-tris-(tert-butyldimethylsilanyloxy)heptanoic acid

(3R,5R,6S)-6-(2-benzyloxy-benzoylamino)-3,5,7-tris-(tert-butyl-dimethyl-silanyloxy)heptanoic acid methyl ester

(3R,5R,6S)-7-benzyloxy-6-benzyloxycarbonylamino-3,5-bis(tert-butyl-dimethylsilanyloxy)-heptanoic acid methyl ester

7-benzyloxy-(6S)-6-benzyloxycarbonylamino-(5R)-5-hydroxy-3-oxoheptanoic acid methyl ester