ethyl (4S,5R,6S)-7-(4-methoxybenzyloxy)-5-(tert-butyldimethylsilyloxy)-4,6-dimethylheptanoate

Base Information

• Chemical Name: ethyl (4S,5R,6S)-7-(4-methoxybenzyloxy)-5-(tert-butyldimethylsilyloxy)-4,6-dimethylheptanoate
• CAS No.: 871236-53-2
• Molecular Formula: C₂₅H₄₄O₅Si
• Molecular Weight: 452.707
• Mol file: 871236-53-2.mol

Synonyms:ethyl (4S,5R,6S)-7-(4-methoxybenzyloxy)-5-(tert-butyldimethylsilyloxy)-4,6-dimethylheptanoate

Chemical Property of ethyl (4S,5R,6S)-7-(4-methoxybenzyloxy)-5-(tert-butyldimethylsilyloxy)-4,6-dimethylheptanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (4S,5R,6S)-7-(4-methoxybenzyloxy)-5-(tert-butyldimethylsilyloxy)-4,6-dimethylheptanoate

There total 7 articles about ethyl (4S,5R,6S)-7-(4-methoxybenzyloxy)-5-(tert-butyldimethylsilyloxy)-4,6-dimethylheptanoate 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: 97.0%

ethyl (4S,5R,6S,2E)-7-(4-methoxybenzyloxy)-5-(tert-butyldimethylsilyloxy)-4,6-dimethylhept-2-enoate (861821-97-8) → ethyl (4S,5R,6S)-7-(4-methoxybenzyloxy)-5-(tert-butyldimethylsilyloxy)-4,6-dimethylheptanoate (871236-53-2)

Guidance literature:

With sodium tetrahydroborate; nickel dichloride; In tetrahydrofuran; methanol; water; at 0 ℃; for 1h;

DOI:10.1021/jm061385k

Reference yield:

2,4-dideoxy-3-O-[(1,1-dimethylethyl)dimethylsilyl]-5-O-[(4-methoxyphenyl)-methyl]-2,4-dimethyl-L-arabinose (212703-47-4) → ethyl (4S,5R,6S)-7-(4-methoxybenzyloxy)-5-(tert-butyldimethylsilyloxy)-4,6-dimethylheptanoate (871236-53-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaH / tetrahydrofuran / cooling

1.2: 8.96 g / tetrahydrofuran / cooling

2.1: 97 percent / NiCl₂*6H₂O; NaBH₄ / methanol; tetrahydrofuran / 0 °C

With sodium tetrahydroborate; sodium hydride; nickel dichloride; In tetrahydrofuran; methanol; 1.2: Horner-Wadsworth-Emmons reaction;

DOI:10.1016/j.tet.2007.05.033

Reference yield:

(-)-(R)-4-benzyl-3-((2R,3S,4S)-3-((tert-butyldimethylsilyl)oxy)-5-((4-methoxybenzyl)oxy)-2,4-dimethylpentanoyl)oxazolidin-2-one (443761-65-7) → ethyl (4S,5R,6S)-7-(4-methoxybenzyloxy)-5-(tert-butyldimethylsilyloxy)-4,6-dimethylheptanoate (871236-53-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 90 percent / LiBH₄ / methanol; tetrahydrofuran / 1.75 h / 0 - 20 °C

2.1: sulfur trioxide*pyridine complex; Et₃N; DMSO / CH₂Cl₂ / 20 °C

3.1: NaH / tetrahydrofuran / cooling

3.2: 8.96 g / tetrahydrofuran / cooling

4.1: 97 percent / NiCl₂*6H₂O; NaBH₄ / methanol; tetrahydrofuran / 0 °C

With sodium tetrahydroborate; lithium borohydride; sodium hydride; dimethyl sulfoxide; triethylamine; nickel dichloride; In tetrahydrofuran; methanol; dichloromethane; 3.2: Horner-Wadsworth-Emmons reaction;

DOI:10.1016/j.tet.2007.05.033

upstream raw materials:

ethyl (4S,5R,6S,2E)-7-(4-methoxybenzyloxy)-5-(tert-butyldimethylsilyloxy)-4,6-dimethylhept-2-enoate

(-)-(R)-4-benzyl-3-((2R,3S,4S)-3-((tert-butyldimethylsilyl)oxy)-5-((4-methoxybenzyl)oxy)-2,4-dimethylpentanoyl)oxazolidin-2-one

t-butyldimethylsiyl triflate

2,4-dideoxy-3-O-[(1,1-dimethylethyl)dimethylsilyl]-5-O-[(4-methoxyphenyl)-methyl]-2,4-dimethyl-L-arabinose

Downstream raw materials:

(4S,5R,6S)-7-(methoxybenzyloxy)-5-(tert-butyldimethylsilyloxy)-4,6-dimethylheptan-1-ol

C₂₃H₄₀O₄Si

(4S,5R,6S)-7-(4-methoxybenzyloxy)-5-(tert-butyldimethylsilyloxy)-4,6-dimethylheptanoic acid

C₄₈H₈₃IO₆Si₂