(R)-4-((2S,4S)-4-(4-methoxybenzyloxy)-6-hydroxy-5,5-dimethyl-tetrahydro-2H-pyran-2-yl)-3-(tert-butyldimethylsilyloxy)-N-phenylbutanamide

Base Information

• Chemical Name: (R)-4-((2S,4S)-4-(4-methoxybenzyloxy)-6-hydroxy-5,5-dimethyl-tetrahydro-2H-pyran-2-yl)-3-(tert-butyldimethylsilyloxy)-N-phenylbutanamide
• CAS No.: 215876-08-7
• Molecular Formula: C₃₁H₄₇NO₆Si
• Molecular Weight: 557.803
• Mol file: 215876-08-7.mol

Synonyms:(R)-4-((2S,4S)-4-(4-methoxybenzyloxy)-6-hydroxy-5,5-dimethyl-tetrahydro-2H-pyran-2-yl)-3-(tert-butyldimethylsilyloxy)-N-phenylbutanamide

Chemical Property of (R)-4-((2S,4S)-4-(4-methoxybenzyloxy)-6-hydroxy-5,5-dimethyl-tetrahydro-2H-pyran-2-yl)-3-(tert-butyldimethylsilyloxy)-N-phenylbutanamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-4-((2S,4S)-4-(4-methoxybenzyloxy)-6-hydroxy-5,5-dimethyl-tetrahydro-2H-pyran-2-yl)-3-(tert-butyldimethylsilyloxy)-N-phenylbutanamide

There total 14 articles about (R)-4-((2S,4S)-4-(4-methoxybenzyloxy)-6-hydroxy-5,5-dimethyl-tetrahydro-2H-pyran-2-yl)-3-(tert-butyldimethylsilyloxy)-N-phenylbutanamide 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: 89.0%

(3R,5S,7S)-7-(4-methoxybenzyloxy)-3-(tert-butyldimethylsilyloxy)-5-hydroxy-8,8-dimethyl-N-phenyldec-9-enamide (1173194-11-0) → (R)-4-((2S,4S)-4-(4-methoxybenzyloxy)-6-hydroxy-5,5-dimethyl-tetrahydro-2H-pyran-2-yl)-3-(tert-butyldimethylsilyloxy)-N-phenylbutanamide (215876-08-7)

Guidance literature:

(3R,5S,7S)-7-(4-methoxybenzyloxy)-3-(tert-butyldimethylsilyloxy)-5-hydroxy-8,8-dimethyl-N-phenyldec-9-enamide; With ozone; In dichloromethane; at -78 ℃;

With triphenylphosphine; In dichloromethane; at 0 - 25 ℃; Inert atmosphere;

DOI:10.1021/ol901096d

Reference yield: 72.0%

(3R,5S,7S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-hydroxy-7-(4-methoxy-benzyloxy)-8,8-dimethyl-10,10-diphenyl-dec-9-enoic acid phenylamide (247146-15-2) → (R)-4-((2S,4S)-4-(4-methoxybenzyloxy)-6-hydroxy-5,5-dimethyl-tetrahydro-2H-pyran-2-yl)-3-(tert-butyldimethylsilyloxy)-N-phenylbutanamide (215876-08-7) + (3R,5S,7S)-3-(tert-Butyl-dimethyl-silanyloxy)-8-(3,3-diphenyl-oxiranyl)-5-hydroxy-7-(4-methoxy-benzyloxy)-8-methyl-nonanoic acid phenylamide + 4-Methoxy-benzoic acid (1S,3S,5R)-5-(tert-butyl-dimethyl-silanyloxy)-1-(1,1-dimethyl-3,3-diphenyl-propyl)-3-hydroxy-6-phenylcarbamoyl-hexyl ester

Guidance literature:

(3R,5S,7S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-hydroxy-7-(4-methoxy-benzyloxy)-8,8-dimethyl-10,10-diphenyl-dec-9-enoic acid phenylamide; With ozone; In methanol; dichloromethane; at -78 ℃;

With dimethylsulfide; In methanol; dichloromethane;

DOI:10.1021/ja990860j

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → (R)-4-((2S,4S)-4-(4-methoxybenzyloxy)-6-hydroxy-5,5-dimethyl-tetrahydro-2H-pyran-2-yl)-3-(tert-butyldimethylsilyloxy)-N-phenylbutanamide (215876-08-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 64 percent / 2,6-lutidine / CH₂Cl₂ / -10 °C

2.1: Me₃Al / CH₂Cl₂ / 30 °C

2.2: 75 percent / CH₂Cl₂ / 0 °C

3.1: O₃ / CH₂Cl₂; methanol / -78 °C

3.2: 72 percent / Me₂S / CH₂Cl₂; methanol

With 2,6-dimethylpyridine; trimethylaluminum; ozone; In methanol; dichloromethane; 1.1: silylation / 2.1: trimethylalumination / 2.2: Ring cleavage / 3.1: ozonolysis / 3.2: Reduction;

DOI:10.1021/ja990860j

upstream raw materials:

(3R,5S,7S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-hydroxy-7-(4-methoxy-benzyloxy)-8,8-dimethyl-10,10-diphenyl-dec-9-enoic acid phenylamide

t-butyldimethylsiyl triflate

(S)-3-(4-Methoxy-benzyloxy)-4,4-dimethyl-6,6-diphenyl-hex-5-enal

(4R,6R)-4-Hydroxy-6-[(S)-2-(4-methoxy-benzyloxy)-3,3-dimethyl-5,5-diphenyl-pent-4-enyl]-tetrahydro-pyran-2-one

Downstream raw materials:

(R)-4-[(2S,4S,6R)-6-Benzenesulfonyl-4-(4-methoxy-benzyloxy)-5,5-dimethyl-tetrahydro-pyran-2-yl]-3-(tert-butyl-dimethyl-silanyloxy)-N-phenyl-butyramide

(R)-3-(tert-Butyl-dimethyl-silanyloxy)-4-[(2S,4S,6R)-4-(4-methoxy-benzyloxy)-5,5-dimethyl-6-phenylsulfanyl-tetrahydro-pyran-2-yl]-N-phenyl-butyramide

C₇₁H₁₁₅NO₁₂Si₃

C₇₇H₁₂₉NO₁₂Si₄