(2R,3R,4R)-(E)-5-((tert-butyldimethylsilyl)oxy)pent-2-en-1-yl 3-hydroxy-4-((4-methoxybenzyl)oxy)-2,6-dimethylhept-6-enoate

Base Information

Chemical Name:(2R,3R,4R)-(E)-5-((tert-butyldimethylsilyl)oxy)pent-2-en-1-yl 3-hydroxy-4-((4-methoxybenzyl)oxy)-2,6-dimethylhept-6-enoate
CAS No.:1598415-37-2
Molecular Formula:C₂₉H₄₈O₆Si
Molecular Weight:520.782
Hs Code.:

Synonyms:(2R,3R,4R)-(E)-5-((tert-butyldimethylsilyl)oxy)pent-2-en-1-yl 3-hydroxy-4-((4-methoxybenzyl)oxy)-2,6-dimethylhept-6-enoate

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Chemical Property of (2R,3R,4R)-(E)-5-((tert-butyldimethylsilyl)oxy)pent-2-en-1-yl 3-hydroxy-4-((4-methoxybenzyl)oxy)-2,6-dimethylhept-6-enoate

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Technology Process of (2R,3R,4R)-(E)-5-((tert-butyldimethylsilyl)oxy)pent-2-en-1-yl 3-hydroxy-4-((4-methoxybenzyl)oxy)-2,6-dimethylhept-6-enoate

There total 5 articles about (2R,3R,4R)-(E)-5-((tert-butyldimethylsilyl)oxy)pent-2-en-1-yl 3-hydroxy-4-((4-methoxybenzyl)oxy)-2,6-dimethylhept-6-enoate 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: 59.0%

: 1598415-36-1
(2R,3R,4R)-1-((R)-4-benzyl-2-thioxothiazolidin-3-yl)-3-hydroxy-4-((4-methoxybenzyl)oxy)-2,6-dimethylhept-6-en-1-one

: 468745-31-5
(2E)-2-methyl-5-[((1,1-dimethyl)ethyl)dimethylsilyloxy]pent-2-en-1-ol

: 1598415-37-2
(2R,3R,4R)-(E)-5-((tert-butyldimethylsilyl)oxy)pent-2-en-1-yl 3-hydroxy-4-((4-methoxybenzyl)oxy)-2,6-dimethylhept-6-enoate

Guidance literature:: With 1H-imidazole; dmap; In dichloromethane; at 20 ℃; for 72h;
DOI:10.1021/ol5008422

Reference yield:

: 1598415-33-8
C₂₀H₂₇NO₅

: 1598415-37-2
(2R,3R,4R)-(E)-5-((tert-butyldimethylsilyl)oxy)pent-2-en-1-yl 3-hydroxy-4-((4-methoxybenzyl)oxy)-2,6-dimethylhept-6-enoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium tetrahydroborate / water; tetrahydrofuran / 2 h / 0 °C

2.1: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane / 2.42 h / -78 - 0 °C / Inert atmosphere

3.1: titanium tetrachloride / dichloromethane / 0.25 h / Cooling with ice

3.2: 0.75 h / -78 - 0 °C

3.3: 13 h / -78 - -20 °C

4.1: 1H-imidazole; dmap / dichloromethane / 72 h / 20 °C

With 1H-imidazole; dmap; sodium tetrahydroborate; oxalyl dichloride; titanium tetrachloride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; water; 2.1: |Swern Oxidation / 3.1: |Aldol Condensation / 3.2: |Aldol Condensation / 3.3: |Aldol Condensation;
DOI:10.1021/ol5008422

Reference yield:

: 1598415-34-9
(R)-2-((4-methoxybenzyl)oxy)-4-methylpent-4-en-1-ol

: 1598415-37-2
(2R,3R,4R)-(E)-5-((tert-butyldimethylsilyl)oxy)pent-2-en-1-yl 3-hydroxy-4-((4-methoxybenzyl)oxy)-2,6-dimethylhept-6-enoate

Guidance literature:: Multi-step reaction with 3 steps

1.1: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane / 2.42 h / -78 - 0 °C / Inert atmosphere

2.1: titanium tetrachloride / dichloromethane / 0.25 h / Cooling with ice

2.2: 0.75 h / -78 - 0 °C

2.3: 13 h / -78 - -20 °C

3.1: 1H-imidazole; dmap / dichloromethane / 72 h / 20 °C

With 1H-imidazole; dmap; oxalyl dichloride; titanium tetrachloride; dimethyl sulfoxide; triethylamine; In dichloromethane; 1.1: |Swern Oxidation / 2.1: |Aldol Condensation / 2.2: |Aldol Condensation / 2.3: |Aldol Condensation;
DOI:10.1021/ol5008422