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

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Chemical Name:(2R,3R,4R)-1-((R)-4-benzyl-2-thioxothiazolidin-3-yl)-3-hydroxy-4-((4-methoxybenzyl)oxy)-2,6-dimethylhept-6-en-1-one
CAS No.:1598415-36-1
Molecular Formula:C₂₇H₃₃NO₄S₂
Molecular Weight:499.695
Hs Code.:

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

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Chemical Property of (2R,3R,4R)-1-((R)-4-benzyl-2-thioxothiazolidin-3-yl)-3-hydroxy-4-((4-methoxybenzyl)oxy)-2,6-dimethylhept-6-en-1-one

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Technology Process of (2R,3R,4R)-1-((R)-4-benzyl-2-thioxothiazolidin-3-yl)-3-hydroxy-4-((4-methoxybenzyl)oxy)-2,6-dimethylhept-6-en-1-one

There total 4 articles about (2R,3R,4R)-1-((R)-4-benzyl-2-thioxothiazolidin-3-yl)-3-hydroxy-4-((4-methoxybenzyl)oxy)-2,6-dimethylhept-6-en-1-one 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:

: 863324-53-2
(R)-1-(4-benzyl-2-thioxothiazolidin-3-yl)propan-1-one

: 1598415-35-0
(R)-2-((4-methoxybenzyl)oxy)-4-methylpent-4-enal

: 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

: C₂₇H₃₃NO₄S₂

Guidance literature:: (R)-1-(4-benzyl-2-thioxothiazolidin-3-yl)propan-1-one; With titanium tetrachloride; In dichloromethane; for 0.25h; Cooling with ice;

With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; dichloromethane; at -78 - 0 ℃; for 0.75h;

(R)-2-((4-methoxybenzyl)oxy)-4-methylpent-4-enal; In 1-methyl-pyrrolidin-2-one; dichloromethane; at -78 - -20 ℃; for 13h; Overall yield = 81 %; Overall yield = 3.41 g;
DOI:10.1021/ol5008422

Reference yield:

: 1598415-33-8
C₂₀H₂₇NO₅

: 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

: C₂₇H₃₃NO₄S₂

Guidance literature:: Multi-step reaction with 3 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

With 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

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

: C₂₇H₃₃NO₄S₂

Guidance literature:: Multi-step reaction with 2 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

With 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