(3R,4R,5S)-5-((tert-butyldimethylsilyl)oxy)-1-((4-methoxybenzyl)oxy)hept-6-ene-3,4-diol

Base Information

Chemical Name:(3R,4R,5S)-5-((tert-butyldimethylsilyl)oxy)-1-((4-methoxybenzyl)oxy)hept-6-ene-3,4-diol
CAS No.:1610954-25-0
Molecular Formula:C₂₁H₃₆O₅Si
Molecular Weight:396.599
Hs Code.:

Synonyms:(3R,4R,5S)-5-((tert-butyldimethylsilyl)oxy)-1-((4-methoxybenzyl)oxy)hept-6-ene-3,4-diol

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Chemical Property of (3R,4R,5S)-5-((tert-butyldimethylsilyl)oxy)-1-((4-methoxybenzyl)oxy)hept-6-ene-3,4-diol

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Technology Process of (3R,4R,5S)-5-((tert-butyldimethylsilyl)oxy)-1-((4-methoxybenzyl)oxy)hept-6-ene-3,4-diol

There total 6 articles about (3R,4R,5S)-5-((tert-butyldimethylsilyl)oxy)-1-((4-methoxybenzyl)oxy)hept-6-ene-3,4-diol 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: 82.0%

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

: 1610954-25-0
(3R,4R,5S)-5-((tert-butyldimethylsilyl)oxy)-1-((4-methoxybenzyl)oxy)hept-6-ene-3,4-diol

Guidance literature:: With methanol; potassium carbonate; at 0 - 20 ℃; for 3h;
DOI:10.1016/j.tetlet.2014.04.068

Reference yield:

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

: 1610954-25-0
(3R,4R,5S)-5-((tert-butyldimethylsilyl)oxy)-1-((4-methoxybenzyl)oxy)hept-6-ene-3,4-diol

Guidance literature:: Multi-step reaction with 6 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

6: potassium carbonate; methanol / 3 h / 0 - 20 °C

With 1H-imidazole; titanium(IV) isopropylate; methanol; tert.-butylhydroperoxide; L-(+)-diisopropyl tartrate; potassium carbonate; 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

: 1610954-25-0
(3R,4R,5S)-5-((tert-butyldimethylsilyl)oxy)-1-((4-methoxybenzyl)oxy)hept-6-ene-3,4-diol

Guidance literature:: Multi-step reaction with 4 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

4: potassium carbonate; methanol / 3 h / 0 - 20 °C

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