(-)-(2S,3R,4S)-3-((tert-butyldimethylsilyl)oxy)-5-((4-methoxybenzyl)oxy)-2,4-dimethylpentan-1-ol

Base Information

• Chemical Name: (-)-(2S,3R,4S)-3-((tert-butyldimethylsilyl)oxy)-5-((4-methoxybenzyl)oxy)-2,4-dimethylpentan-1-ol
• CAS No.: 792911-22-9
• Molecular Formula: C₂₁H₃₈O₄Si
• Molecular Weight: 382.616

Synonyms:(-)-(2S,3R,4S)-3-((tert-butyldimethylsilyl)oxy)-5-((4-methoxybenzyl)oxy)-2,4-dimethylpentan-1-ol

Chemical Property of (-)-(2S,3R,4S)-3-((tert-butyldimethylsilyl)oxy)-5-((4-methoxybenzyl)oxy)-2,4-dimethylpentan-1-ol

Chemical Property:

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Technology Process of (-)-(2S,3R,4S)-3-((tert-butyldimethylsilyl)oxy)-5-((4-methoxybenzyl)oxy)-2,4-dimethylpentan-1-ol

There total 7 articles about (-)-(2S,3R,4S)-3-((tert-butyldimethylsilyl)oxy)-5-((4-methoxybenzyl)oxy)-2,4-dimethylpentan-1-ol 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: 100.0%

(2R,3S,4S)-1-((R)-4'-benzyl-2-thioxothiazolidin-3-yl)-3-(tert-butyldimethylsilyloxy)-5-(4''-methoxybenzyloxy)-2,4-dimethylpentan-1-one (1037198-33-6) → (-)-(2S,3R,4S)-3-((tert-butyldimethylsilyl)oxy)-5-((4-methoxybenzyl)oxy)-2,4-dimethylpentan-1-ol (792911-22-9)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; methanol; diethyl ether; at 0 - 20 ℃;

DOI:10.1016/j.tet.2008.02.109

Reference yield: 93.0%

(2S,3S,4S)-1,3-bis[(tert-butyldimethylsilyl)oxy]-5-[(4-Methoxybenzyl)oxy]-2,4-dimethylpentane (792911-21-8) → (-)-(2S,3R,4S)-3-((tert-butyldimethylsilyl)oxy)-5-((4-methoxybenzyl)oxy)-2,4-dimethylpentan-1-ol (792911-22-9)

Guidance literature:

With toluene-4-sulfonic acid; In tetrahydrofuran; water; for 24h;

DOI:10.1002/anie.200460589

Reference yield: 90.0%

(-)-(R)-4-benzyl-3-((2R,3S,4S)-3-((tert-butyldimethylsilyl)oxy)-5-((4-methoxybenzyl)oxy)-2,4-dimethylpentanoyl)oxazolidin-2-one (443761-65-7) → (-)-(2S,3R,4S)-3-((tert-butyldimethylsilyl)oxy)-5-((4-methoxybenzyl)oxy)-2,4-dimethylpentan-1-ol (792911-22-9)

Guidance literature:

With lithium borohydride; In tetrahydrofuran; methanol; at 0 - 20 ℃; for 1.75h;

DOI:10.1016/j.tet.2007.05.033

upstream raw materials:

(2S,3S,4S)-1,3-bis[(tert-butyldimethylsilyl)oxy]-5-[(4-Methoxybenzyl)oxy]-2,4-dimethylpentane

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

t-butyldimethylsiyl triflate

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

Downstream raw materials:

1-((2S,3R,4S)-3,7-bis(tert-butyldimethylsilyloxy)-2,4-dimethylheptyloxy)methyl-4-methoxybenzene

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

(3Z,9E)-(5S,6S,7R,11R,13S,14R,15S)-14-(tert-Butyl-dimethyl-silanyloxy)-6,16-bis-(4-methoxy-benzyloxy)-5,7,11,13,15-pentamethyl-hexadeca-1,3,9-trien-8-one

(2R,4S,5R,6S)-7-(4-methoxybenzyloxy)-5-(tert-butyldimethylsilyloxy)-2,4,6-trimethylheptanal

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