(3R,4R,5S)-5-((tert-butyldimethylsilyl)oxy)-4-hydroxy-1-((4-methoxybenzyl)oxy)hept-6-en-3-yl benzoate

Base Information

Chemical Name:(3R,4R,5S)-5-((tert-butyldimethylsilyl)oxy)-4-hydroxy-1-((4-methoxybenzyl)oxy)hept-6-en-3-yl benzoate
CAS No.:1610954-24-9
Molecular Formula:C₂₈H₄₀O₆Si
Molecular Weight:500.707
Hs Code.:

Synonyms:(3R,4R,5S)-5-((tert-butyldimethylsilyl)oxy)-4-hydroxy-1-((4-methoxybenzyl)oxy)hept-6-en-3-yl benzoate

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Chemical Property of (3R,4R,5S)-5-((tert-butyldimethylsilyl)oxy)-4-hydroxy-1-((4-methoxybenzyl)oxy)hept-6-en-3-yl benzoate

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Technology Process of (3R,4R,5S)-5-((tert-butyldimethylsilyl)oxy)-4-hydroxy-1-((4-methoxybenzyl)oxy)hept-6-en-3-yl benzoate

There total 5 articles about (3R,4R,5S)-5-((tert-butyldimethylsilyl)oxy)-4-hydroxy-1-((4-methoxybenzyl)oxy)hept-6-en-3-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: 86.0%

: 1610954-23-8
(3R,4S,5S)-4,5-dihydroxy-1-((4-methoxybenzyl)oxy)hept-6-en-3-yl benzoate

: 18162-48-6
tert-butyldimethylsilyl chloride

: 1610954-24-9
(3R,4R,5S)-5-((tert-butyldimethylsilyl)oxy)-4-hydroxy-1-((4-methoxybenzyl)oxy)hept-6-en-3-yl benzoate

Guidance literature:: With 1H-imidazole; In dichloromethane; at 0 - 20 ℃; for 4h;
DOI:10.1016/j.tetlet.2014.04.068

Reference yield:

: 158817-21-1
(E)-5-(4-methoxybenzyloxy)pent-2-en-1-ol

: 1610954-24-9
(3R,4R,5S)-5-((tert-butyldimethylsilyl)oxy)-4-hydroxy-1-((4-methoxybenzyl)oxy)hept-6-en-3-yl benzoate

Guidance literature:: Multi-step reaction with 5 steps

1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide; dichloromethane / 1 h / 0 - 20 °C

2: dimethyl sulfoxide; dichloromethane; tetrahydrofuran / 1 h / 0 - 20 °C

3: L-(+)-diisopropyl tartrate; titanium(IV) isopropylate; tert.-butylhydroperoxide / dichloromethane / 18 h / -20 °C / Molecular sieve

4: titanium(IV) isopropylate / dichloromethane / 5 h / 0 - 20 °C

5: 1H-imidazole / dichloromethane / 4 h / 0 - 20 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; L-(+)-diisopropyl tartrate; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; 3: |Sharpless Asymmetric Epoxidation;
DOI:10.1016/j.tetlet.2014.04.068

Reference yield:

: 1610954-48-7
(E)-7-((4-methoxybenzyl)oxy)hepta-1,4-dien-3-ol

: 1610954-24-9
(3R,4R,5S)-5-((tert-butyldimethylsilyl)oxy)-4-hydroxy-1-((4-methoxybenzyl)oxy)hept-6-en-3-yl benzoate

Guidance literature:: Multi-step reaction with 3 steps

1: L-(+)-diisopropyl tartrate; titanium(IV) isopropylate; tert.-butylhydroperoxide / dichloromethane / 18 h / -20 °C / Molecular sieve

2: titanium(IV) isopropylate / dichloromethane / 5 h / 0 - 20 °C

3: 1H-imidazole / dichloromethane / 4 h / 0 - 20 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; L-(+)-diisopropyl tartrate; In dichloromethane; 1: |Sharpless Asymmetric Epoxidation;
DOI:10.1016/j.tetlet.2014.04.068