(1S,3aR,14bS)-2-methoxy-1,5,6,8,9,14b-hexahydro-4H-[1,3]dioxolo[4',5':4,5]benzo[1,2-d]cyclopenta[b]pyrrolo[1,2-a]azepin-1-yl (R)-2-((E)-4-(benzyloxy)-4-methylpent-2-en-1-yl)-4-oxooxetane-2-carboxylate

Base Information

• Chemical Name: (1S,3aR,14bS)-2-methoxy-1,5,6,8,9,14b-hexahydro-4H-[1,3]dioxolo[4',5':4,5]benzo[1,2-d]cyclopenta[b]pyrrolo[1,2-a]azepin-1-yl (R)-2-((E)-4-(benzyloxy)-4-methylpent-2-en-1-yl)-4-oxooxetane-2-carboxylate
• CAS No.: 1040272-38-5
• Molecular Formula: C₃₅H₃₉NO₈
• Molecular Weight: 601.697
• Mol file: 1040272-38-5.mol

Synonyms:(1S,3aR,14bS)-2-methoxy-1,5,6,8,9,14b-hexahydro-4H-[1,3]dioxolo[4',5':4,5]benzo[1,2-d]cyclopenta[b]pyrrolo[1,2-a]azepin-1-yl (R)-2-((E)-4-(benzyloxy)-4-methylpent-2-en-1-yl)-4-oxooxetane-2-carboxylate

Chemical Property of (1S,3aR,14bS)-2-methoxy-1,5,6,8,9,14b-hexahydro-4H-[1,3]dioxolo[4',5':4,5]benzo[1,2-d]cyclopenta[b]pyrrolo[1,2-a]azepin-1-yl (R)-2-((E)-4-(benzyloxy)-4-methylpent-2-en-1-yl)-4-oxooxetane-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,3aR,14bS)-2-methoxy-1,5,6,8,9,14b-hexahydro-4H-[1,3]dioxolo[4',5':4,5]benzo[1,2-d]cyclopenta[b]pyrrolo[1,2-a]azepin-1-yl (R)-2-((E)-4-(benzyloxy)-4-methylpent-2-en-1-yl)-4-oxooxetane-2-carboxylate

There total 27 articles about (1S,3aR,14bS)-2-methoxy-1,5,6,8,9,14b-hexahydro-4H-[1,3]dioxolo[4',5':4,5]benzo[1,2-d]cyclopenta[b]pyrrolo[1,2-a]azepin-1-yl (R)-2-((E)-4-(benzyloxy)-4-methylpent-2-en-1-yl)-4-oxooxetane-2-carboxylate 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: 97.0%

(R,E)-2-(4-(benzyloxy)-4-methylpent-2-enyl)-4-oxooxetane-2-carboxylic acid (1040272-12-5) + cephalotaxine (24316-19-6) → (1S,3aR,14bS)-2-methoxy-1,5,6,8,9,14b-hexahydro-4H-[1,3]dioxolo[4',5':4,5]benzo[1,2-d]cyclopenta[b]pyrrolo[1,2-a]azepin-1-yl (R)-2-((E)-4-(benzyloxy)-4-methylpent-2-en-1-yl)-4-oxooxetane-2-carboxylate (1040272-38-5)

Guidance literature:

(R,E)-2-(4-(benzyloxy)-4-methylpent-2-enyl)-4-oxooxetane-2-carboxylic acid; With 2,4,6-trichlorobenzoyl chloride; triethylamine; In dichloromethane; at 23 ℃; for 1h; Inert atmosphere;

cephalotaxine; With dmap; In dichloromethane; at 23 ℃; for 0.416667h; Inert atmosphere;

Reference yield:

C21H27NO5Si (910138-80-6) → (1S,3aR,14bS)-2-methoxy-1,5,6,8,9,14b-hexahydro-4H-[1,3]dioxolo[4',5':4,5]benzo[1,2-d]cyclopenta[b]pyrrolo[1,2-a]azepin-1-yl (R)-2-((E)-4-(benzyloxy)-4-methylpent-2-en-1-yl)-4-oxooxetane-2-carboxylate (1040272-38-5)

Guidance literature:

Multi-step reaction with 12 steps

1.1: silver trifluoromethanesulfonate / dichloromethane / 1 h / 25 °C / Inert atmosphere

1.2: -45 - 25 °C

2.1: tert-butyl alcohol / tetrahydrofuran / 0.17 h / 25 °C / Inert atmosphere

2.2: 0.17 h / -78 °C / Inert atmosphere

2.3: -78 - 25 °C / Inert atmosphere

3.1: Schwartz's reagent / tetrahydrofuran / 16 h / 25 - 40 °C / Inert atmosphere

4.1: potassium hexamethylsilazane / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere

4.2: 1 h / 0 °C / Inert atmosphere

5.1: hydrogenchloride / methanol; water / 16 h / 25 °C / Inert atmosphere

6.1: ytterbium(III) triflate / dichloromethane / 48 h / 0 °C / Inert atmosphere

7.1: 2-iodoxybenzoic acid / dimethyl sulfoxide / 20 h / 25 °C / Inert atmosphere

8.1: chromium dichloride / water / 1 h / 25 °C / Inert atmosphere

9.1: hydrogen / palladium on activated charcoal / ethyl acetate / 6 h / 25 °C

10.1: toluene-4-sulfonic acid / dichloromethane / 0 - 25 °C / Inert atmosphere

11.1: sodium tetrahydroborate / methanol / -78 - 25 °C / Inert atmosphere

12.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / dichloromethane / 1 h / 23 °C / Inert atmosphere

12.2: 0.42 h / 23 °C / Inert atmosphere

With chromium dichloride; hydrogenchloride; sodium tetrahydroborate; Schwartz's reagent; 2,4,6-trichlorobenzoyl chloride; 2-iodoxybenzoic acid; hydrogen; silver trifluoromethanesulfonate; potassium hexamethylsilazane; toluene-4-sulfonic acid; triethylamine; ytterbium(III) triflate; tert-butyl alcohol; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; ethyl acetate;

Reference yield:

C25H31NO6 (910138-82-8) → (1S,3aR,14bS)-2-methoxy-1,5,6,8,9,14b-hexahydro-4H-[1,3]dioxolo[4',5':4,5]benzo[1,2-d]cyclopenta[b]pyrrolo[1,2-a]azepin-1-yl (R)-2-((E)-4-(benzyloxy)-4-methylpent-2-en-1-yl)-4-oxooxetane-2-carboxylate (1040272-38-5)

Guidance literature:

Multi-step reaction with 10 steps

1.1: Schwartz's reagent / tetrahydrofuran / 16 h / 25 - 40 °C / Inert atmosphere

2.1: potassium hexamethylsilazane / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere

2.2: 1 h / 0 °C / Inert atmosphere

3.1: hydrogenchloride / methanol; water / 16 h / 25 °C / Inert atmosphere

4.1: ytterbium(III) triflate / dichloromethane / 48 h / 0 °C / Inert atmosphere

5.1: 2-iodoxybenzoic acid / dimethyl sulfoxide / 20 h / 25 °C / Inert atmosphere

6.1: chromium dichloride / water / 1 h / 25 °C / Inert atmosphere

7.1: hydrogen / palladium on activated charcoal / ethyl acetate / 6 h / 25 °C

8.1: toluene-4-sulfonic acid / dichloromethane / 0 - 25 °C / Inert atmosphere

9.1: sodium tetrahydroborate / methanol / -78 - 25 °C / Inert atmosphere

10.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / dichloromethane / 1 h / 23 °C / Inert atmosphere

10.2: 0.42 h / 23 °C / Inert atmosphere

With chromium dichloride; hydrogenchloride; sodium tetrahydroborate; Schwartz's reagent; 2,4,6-trichlorobenzoyl chloride; 2-iodoxybenzoic acid; hydrogen; potassium hexamethylsilazane; toluene-4-sulfonic acid; triethylamine; ytterbium(III) triflate; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; ethyl acetate;

upstream raw materials:

(R,E)-2-(4-(benzyloxy)-4-methylpent-2-enyl)-4-oxooxetane-2-carboxylic acid

cephalotaxine

C₁₇H₁₇NO₅

C₂₀H₂₃NO₅

Downstream raw materials:

1-((1S,3aR,14bS)-2-methoxy-1,5,6,8,9,14b-hexahydro-4H-[1,3]dioxolo[4',5':4,5]benzo[1,2-d]cyclopenta[b]pyrrolo[1,2-a]azepin-1-yl) 4-methyl (R)-2-((E)-4-(benzyloxy)-4-methylpent-2-en-1-yl)-2-hydroxysuccinate

homoharringtonine