3-Deoxy-3-oxocephalotaxine

Base Information

• Chemical Name: 3-Deoxy-3-oxocephalotaxine
• CAS No.: 38750-57-1
• Molecular Formula: C₁₈H₁₉NO₄
• Molecular Weight: 313.353
• Mol file: 38750-57-1.mol

Synonyms:(3aR)-2-methoxy-(3arC4,14bc)-5,6,9,14b-tetrahydro-4H,8H-cyclopenta[b][1,3]dioxolo[4',5':4,5]benzo[1,2-d]pyrrolo[1,2-a]azepin-1-one;3-oxo-deoxycephalotaxine;Cephalotaxinon;cephalotaxinone;(-)-cephalotaxinone;

Chemical Property of 3-Deoxy-3-oxocephalotaxine

Chemical Property:

• PSA: 48.00000
• LogP: 1.94050

Purity/Quality:

98.5% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3-Deoxy-3-oxocephalotaxine

There total 89 articles about 3-Deoxy-3-oxocephalotaxine 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%

Trimethylmethoxysilane (1825-61-2) + (±)-demethylcephalotaxinone (38848-25-8) → (±)-cephalotaxinone (38750-57-1,38848-26-9)

Guidance literature:

With trifluorormethanesulfonic acid; In dichloromethane; at 0 - 40 ℃; Inert atmosphere;

DOI:10.1021/acs.orglett.5b02106

Reference yield: 84.0%

(±)-demethylcephalotaxinone (38848-25-8) + 2,2-dimethoxy-propane (77-76-9) → (±)-cephalotaxinone (38750-57-1,38848-26-9)

Guidance literature:

With toluene-4-sulfonic acid; In 1,4-dioxane; for 22.5h; Heating;

Reference yield: 60.0%

33-methoxy-7-aza-1(5,6)-benzo[d] [1,3]dioxola-3(2,5)-furanacyclononaphane → (±)-cephalotaxinone (38750-57-1,38848-26-9)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 2,2,2-trifluoroethanol; at 50 ℃; for 15h; Inert atmosphere;

DOI:10.1002/anie.201902174

upstream raw materials:

cephalotaxine

(3aS)-5,6,8,9-Tetrahydro-1-hydroxy-4H-cyclopenta<1,3>dioxolo<4,5-h>pyrrolo<2,1-b><3>benzazepin-2(3H)-one

trimethyl orthoformate

6-chloro-2,2-dimethyl-3a,6a-dihydro-cyclopenta[1,3]dioxol-4-one

Downstream raw materials:

(±)-cephalotaxine

(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

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

Refernces

• 1、 Paudler,McKay. "The structures of some of the minor alkaloids of Cephalotaxus fortunei.". . p. 2110 - 2112. Retrieved 1973.
• 2、 Powell,R.G.,Mikolajczak,K.L.. "-". . p. 2987 - 2991. Retrieved 1973.
• 3、 -. "ANALOGUES AND DERIVATIVES OF CEPHALOTAXINE AND METHODS FOR MAKING AND USING THE COMPOUNDS". Page/Page column 47; 52. . Retrieved 2020/09/30.
• 4、 Liu, Hao,Yu, Jing,Li, Xinyu,Yan, Rui,Xiao, Ji-Chang,Hong, Ran. "Stereoselectivity in N-Iminium Ion Cyclization: Development of an Efficient Synthesis of (±)-Cephalotaxine". . p. 4444 - 4447. Retrieved 2015/09/28.