(3-methyl-butyl)-butenedioic acid 1-((3aR)-2-methoxy-(3arC⁴,14bc)-1,5,6,8,9,14b-hexahydro-4H-cyclopenta[b][1,3]dioxolo[4',5':4,5]benzo[1,2-d]pyrrolo[1,2-a]azepin-1t-yl) ester 4-methyl ester

Base Information

• Chemical Name: (3-methyl-butyl)-butenedioic acid 1-((3aR)-2-methoxy-(3arC⁴,14bc)-1,5,6,8,9,14b-hexahydro-4H-cyclopenta[b][1,3]dioxolo[4',5':4,5]benzo[1,2-d]pyrrolo[1,2-a]azepin-1t-yl) ester 4-methyl ester
• CAS No.: 54086-27-0
• Molecular Formula: C₂₈H₃₅NO₇
• Molecular Weight: 497.588

Synonyms:

Chemical Property of (3-methyl-butyl)-butenedioic acid 1-((3aR)-2-methoxy-(3arC⁴,14bc)-1,5,6,8,9,14b-hexahydro-4H-cyclopenta[b][1,3]dioxolo[4',5':4,5]benzo[1,2-d]pyrrolo[1,2-a]azepin-1t-yl) ester 4-methyl ester

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Technology Process of (3-methyl-butyl)-butenedioic acid 1-((3aR)-2-methoxy-(3arC⁴,14bc)-1,5,6,8,9,14b-hexahydro-4H-cyclopenta[b][1,3]dioxolo[4',5':4,5]benzo[1,2-d]pyrrolo[1,2-a]azepin-1t-yl) ester 4-methyl ester

There total 3 articles about (3-methyl-butyl)-butenedioic acid 1-((3aR)-2-methoxy-(3arC⁴,14bc)-1,5,6,8,9,14b-hexahydro-4H-cyclopenta[b][1,3]dioxolo[4',5':4,5]benzo[1,2-d]pyrrolo[1,2-a]azepin-1t-yl) ester 4-methyl ester 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: 40.0%

[[1-methoxy-2-(trimethylsilyl)ethenyl]oxy]trimethylsilane (32583-40-7) + C25H31NO6 → (3-methyl-butyl)-butenedioic acid 1-((3aR)-2-methoxy-(3arC4,14bc)-1,5,6,8,9,14b-hexahydro-4H-cyclopenta[b][1,3]dioxolo[4',5':4,5]benzo[1,2-d]pyrrolo[1,2-a]azepin-1t-yl) ester 4-methyl ester (54086-27-0) + deoxyharringtonine (36804-95-2)

Guidance literature:

[[1-methoxy-2-(trimethylsilyl)ethenyl]oxy]trimethylsilane; C₂₅H₃₁NO₆; With boron trifluoride diethyl etherate; In dichloromethane; at -25 ℃; for 22h;

With potassium fluoride dihydrate; In acetonitrile; at 70 ℃; for 4h; Temperature; diastereoselective reaction;

DOI:10.1021/acs.orglett.7b00743

Reference yield:

cephalotaxine (24316-19-6) → (3-methyl-butyl)-butenedioic acid 1-((3aR)-2-methoxy-(3arC4,14bc)-1,5,6,8,9,14b-hexahydro-4H-cyclopenta[b][1,3]dioxolo[4',5':4,5]benzo[1,2-d]pyrrolo[1,2-a]azepin-1t-yl) ester 4-methyl ester (54086-27-0) + deoxyharringtonine (36804-95-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 2,4,6-trichlorobenzoyl chloride; pyridine; dmap / dichloromethane / 4 h / 0 °C

2.1: boron trifluoride diethyl etherate / dichloromethane / 22 h / -25 °C

2.2: 4 h / 70 °C

With pyridine; dmap; 2,4,6-trichlorobenzoyl chloride; boron trifluoride diethyl etherate; In dichloromethane; 2.1: |Mukaiyama Aldol Addition;

DOI:10.1021/acs.orglett.7b00743

Reference yield:

5-methyl-2-oxo-hexanoic acid (26395-06-2) → (3-methyl-butyl)-butenedioic acid 1-((3aR)-2-methoxy-(3arC4,14bc)-1,5,6,8,9,14b-hexahydro-4H-cyclopenta[b][1,3]dioxolo[4',5':4,5]benzo[1,2-d]pyrrolo[1,2-a]azepin-1t-yl) ester 4-methyl ester (54086-27-0) + deoxyharringtonine (36804-95-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 2,4,6-trichlorobenzoyl chloride; pyridine; dmap / dichloromethane / 4 h / 0 °C

2.1: boron trifluoride diethyl etherate / dichloromethane / 22 h / -25 °C

2.2: 4 h / 70 °C

With pyridine; dmap; 2,4,6-trichlorobenzoyl chloride; boron trifluoride diethyl etherate; In dichloromethane; 2.1: |Mukaiyama Aldol Addition;

DOI:10.1021/acs.orglett.7b00743

upstream raw materials:

cephalotaxine

[[1-methoxy-2-(trimethylsilyl)ethenyl]oxy]trimethylsilane

5-methyl-2-oxo-hexanoic acid

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