(-)-(2S,4R,5R,6S)-5-((tert-butyldimethylsilyl)oxy)-7-((4-methoxybenzyl)oxy)-4,6-dimethyl-3-oxoheptan-2-yl benzoate

Base Information

• Chemical Name: (-)-(2S,4R,5R,6S)-5-((tert-butyldimethylsilyl)oxy)-7-((4-methoxybenzyl)oxy)-4,6-dimethyl-3-oxoheptan-2-yl benzoate
• CAS No.: 1037197-86-6
• Molecular Formula: C₃₀H₄₄O₆Si
• Molecular Weight: 528.761

Synonyms:(-)-(2S,4R,5R,6S)-5-((tert-butyldimethylsilyl)oxy)-7-((4-methoxybenzyl)oxy)-4,6-dimethyl-3-oxoheptan-2-yl benzoate

Chemical Property of (-)-(2S,4R,5R,6S)-5-((tert-butyldimethylsilyl)oxy)-7-((4-methoxybenzyl)oxy)-4,6-dimethyl-3-oxoheptan-2-yl benzoate

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (-)-(2S,4R,5R,6S)-5-((tert-butyldimethylsilyl)oxy)-7-((4-methoxybenzyl)oxy)-4,6-dimethyl-3-oxoheptan-2-yl benzoate

There total 6 articles about (-)-(2S,4R,5R,6S)-5-((tert-butyldimethylsilyl)oxy)-7-((4-methoxybenzyl)oxy)-4,6-dimethyl-3-oxoheptan-2-yl benzoate 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: 96.0%

(+)-(2S,4R,5R,6S)-5-hydroxy-7-((4-methoxybenzyl)oxy)-4,6-dimethyl-3-oxoheptan-2-yl benzoate (1037197-81-1) + t-butyldimethylsiyl triflate (69739-34-0) → (-)-(2S,4R,5R,6S)-5-((tert-butyldimethylsilyl)oxy)-7-((4-methoxybenzyl)oxy)-4,6-dimethyl-3-oxoheptan-2-yl benzoate (1037197-86-6)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at -78 - 0 ℃;

DOI:10.1016/j.tet.2008.02.109

Reference yield:

methyl (2S)-[(4-methoxybenzyl)oxy]-2-methylpropanoate (132969-71-2) → (-)-(2S,4R,5R,6S)-5-((tert-butyldimethylsilyl)oxy)-7-((4-methoxybenzyl)oxy)-4,6-dimethyl-3-oxoheptan-2-yl benzoate (1037197-86-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: lithium aluminium tetrahydride / tetrahydrofuran / 21 h / -40 - 20 °C / Inert atmosphere

2.1: oxalyl dichloride / dichloromethane; dimethyl sulfoxide / 1.5 h / -78 - 0 °C / Inert atmosphere

3.1: dicyclohexylboron chloride; N,N-dimethyl-ethanamine / diethyl ether / 2 h / -78 - 0 °C / Inert atmosphere

3.2: 19.5 h / -78 - 0 °C / Inert atmosphere

4.1: 2,6-dimethylpyridine / dichloromethane / -78 - 0 °C / Inert atmosphere

With 2,6-dimethylpyridine; lithium aluminium tetrahydride; oxalyl dichloride; N,N-dimethyl-ethanamine; dicyclohexylboron chloride; In tetrahydrofuran; diethyl ether; dichloromethane; dimethyl sulfoxide;

DOI:10.1021/acs.joc.6b03060

Reference yield:

O-(4-methoxybenzyl)-trichloroacetimidate (89238-99-3) → (-)-(2S,4R,5R,6S)-5-((tert-butyldimethylsilyl)oxy)-7-((4-methoxybenzyl)oxy)-4,6-dimethyl-3-oxoheptan-2-yl benzoate (1037197-86-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 10-camphorsulfonic acid / dichloromethane / 20 h / 20 °C / Inert atmosphere

2.1: lithium aluminium tetrahydride / tetrahydrofuran / 21 h / -40 - 20 °C / Inert atmosphere

3.1: oxalyl dichloride / dichloromethane; dimethyl sulfoxide / 1.5 h / -78 - 0 °C / Inert atmosphere

4.1: dicyclohexylboron chloride; N,N-dimethyl-ethanamine / diethyl ether / 2 h / -78 - 0 °C / Inert atmosphere

4.2: 19.5 h / -78 - 0 °C / Inert atmosphere

5.1: 2,6-dimethylpyridine / dichloromethane / -78 - 0 °C / Inert atmosphere

With 2,6-dimethylpyridine; lithium aluminium tetrahydride; oxalyl dichloride; N,N-dimethyl-ethanamine; 10-camphorsulfonic acid; dicyclohexylboron chloride; In tetrahydrofuran; diethyl ether; dichloromethane; dimethyl sulfoxide;

DOI:10.1021/acs.joc.6b03060

upstream raw materials:

(+)-(2S,4R,5R,6S)-5-hydroxy-7-((4-methoxybenzyl)oxy)-4,6-dimethyl-3-oxoheptan-2-yl benzoate

t-butyldimethylsiyl triflate

methyl (2S)-[(4-methoxybenzyl)oxy]-2-methylpropanoate

O-(4-methoxybenzyl)-trichloroacetimidate

Downstream raw materials:

(2S,4S,5R,6S)-5-(tert-butyldimethylsilyloxy)-7-(4'-methoxy-benzyloxy)-4,6-dimethylheptane-2,3-diol

(+)-tert-butyl(((2S,3S,4S)-1-((4-methoxybenzyl)oxy)-2,4-dimethylhex-5-yn-3-yl)oxy)dimethylsilane

(+)-tert-butyl(((2S,3S,4S)-6,6-dibromo-1-((4-methoxybenzyl)-oxy)-2,4-dimethylhex-5-en-3-yl)oxy)dimethylsilane

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