(S)-1,3-diacetoxy-5-(3,4-dimethoxyphenyl)-3-[2H₃]methyl-2-[1,1,2,2,4,4-2H₆]pentane

Base Information

• Chemical Name: (S)-1,3-diacetoxy-5-(3,4-dimethoxyphenyl)-3-[2H₃]methyl-2-[1,1,2,2,4,4-2H₆]pentane
• CAS No.: 610272-83-8
• Molecular Formula: C₁₇H₂₄O₆
• Molecular Weight: 333.303

Synonyms:(S)-1,3-diacetoxy-5-(3,4-dimethoxyphenyl)-3-[2H₃]methyl-2-[1,1,2,2,4,4-2H₆]pentane

Chemical Property of (S)-1,3-diacetoxy-5-(3,4-dimethoxyphenyl)-3-[2H₃]methyl-2-[1,1,2,2,4,4-2H₆]pentane

Chemical Property:

Purity/Quality:

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Technology Process of (S)-1,3-diacetoxy-5-(3,4-dimethoxyphenyl)-3-[2H₃]methyl-2-[1,1,2,2,4,4-2H₆]pentane

There total 3 articles about (S)-1,3-diacetoxy-5-(3,4-dimethoxyphenyl)-3-[2H₃]methyl-2-[1,1,2,2,4,4-2H₆]pentane 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: 99.0%

acetic anhydride (108-24-7) + (S)-5-(3,4-dimethoxyphenyl)-3-[2H3]methyl-2-[1,1,2,2,4,4-2H6]pentane-1,3-diol (610272-82-7) → (S)-1,3-diacetoxy-5-(3,4-dimethoxyphenyl)-3-[2H3]methyl-2-[1,1,2,2,4,4-2H6]pentane (610272-83-8)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 44h;

DOI:10.1016/S0040-4020(03)00983-9

Reference yield:

(3,4-dimethoxyphenyl)[1,1,3,3,3-2H5]acetone (207979-18-8) → (S)-1,3-diacetoxy-5-(3,4-dimethoxyphenyl)-3-[2H3]methyl-2-[1,1,2,2,4,4-2H6]pentane (610272-83-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: NaH / tetrahydrofuran / 1 h / 20 °C

1.2: 59 percent / tetrahydrofuran / 7 h / 20 °C

2.1: 74 percent / lithium aluminum deuteride / diethyl ether / 2.5 h / 0 °C

3.1: 77 percent / titanium tetraisopropoxide; (L)-(+)-diisopropyl tartrate; tert-butyl hydroperoxide / CH₂Cl₂ / 1 h / -25 °C

4.1: 86 percent / lithium aluminum deuteride / tetrahydrofuran / 2.5 h / 20 °C

5.1: 99 percent / DMAP; Et₃N / CH₂Cl₂ / 44 h / 20 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; lithium aluminium deuteride; L-(+)-diisopropyl tartrate; sodium hydride; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; 1.1: Horner-Emmons reaction / 3.1: Sharpless asymmetric epoxidation;

DOI:10.1016/S0040-4020(03)00983-9

Reference yield:

(2S,3S)-2,3-epoxy-5-(3,4-dimethoxyphenyl)-3-[2H3]methyl-2-[1,1,2,4,4-2H5]pentan-1-ol (610272-81-6) → (S)-1,3-diacetoxy-5-(3,4-dimethoxyphenyl)-3-[2H3]methyl-2-[1,1,2,2,4,4-2H6]pentane (610272-83-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / lithium aluminum deuteride / tetrahydrofuran / 2.5 h / 20 °C

2: 99 percent / DMAP; Et₃N / CH₂Cl₂ / 44 h / 20 °C

With dmap; lithium aluminium deuteride; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4020(03)00983-9

upstream raw materials:

acetic anhydride

(S)-5-(3,4-dimethoxyphenyl)-3-[2H₃]methyl-2-[1,1,2,2,4,4-2H₆]pentane-1,3-diol

(3,4-dimethoxyphenyl)[1,1,3,3,3-2H₅]acetone

(2S,3S)-2,3-epoxy-5-(3,4-dimethoxyphenyl)-3-[2H₃]methyl-2-[1,1,2,4,4-2H₅]pentan-1-ol

Downstream raw materials:

(R)-[2H9]mevalonolactone

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