(2R,3R,11bS)-9-Benzyloxy-2-(6-benzyloxy-4,9-dihydro-3H-β-carbolin-1-ylmethyl)-3-ethyl-10-methoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinoline

Base Information

• Chemical Name: (2R,3R,11bS)-9-Benzyloxy-2-(6-benzyloxy-4,9-dihydro-3H-β-carbolin-1-ylmethyl)-3-ethyl-10-methoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinoline
• CAS No.: 106550-20-3
• Molecular Formula: C₄₂H₄₅N₃O₃
• Molecular Weight: 639.838
• Mol file: 106550-20-3.mol

Synonyms:(2R,3R,11bS)-9-Benzyloxy-2-(6-benzyloxy-4,9-dihydro-3H-β-carbolin-1-ylmethyl)-3-ethyl-10-methoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinoline

Chemical Property of (2R,3R,11bS)-9-Benzyloxy-2-(6-benzyloxy-4,9-dihydro-3H-β-carbolin-1-ylmethyl)-3-ethyl-10-methoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinoline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,11bS)-9-Benzyloxy-2-(6-benzyloxy-4,9-dihydro-3H-β-carbolin-1-ylmethyl)-3-ethyl-10-methoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinoline

There total 7 articles about (2R,3R,11bS)-9-Benzyloxy-2-(6-benzyloxy-4,9-dihydro-3H-β-carbolin-1-ylmethyl)-3-ethyl-10-methoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinoline 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: 69.0%

(+/-)-9-benzyloxy-N-<2-(5-benzyloxy-1H-indol-3-yl)ethyl>-3α-ethyl-1,3,4,6,7,11bα-hexahydro-10-methoxy-2H-benzoquinolizine-2β-acetamide (74059-18-0,106622-53-1) → (=/-)-9-benzyloxy-2β-<(6-benzyloxy-4,9-dihydro-3H-pyrido<3,4-b>indol-1-yl)methyl>-3α-ethyl-1,3,4,6,7,11bα-hexahydro-10-methoxy-2H-benzoquinolizine (74059-19-1,106550-20-3)

Guidance literature:

With trichlorophosphate; In toluene; for 2.5h; Heating;

DOI:10.1248/cpb.33.3724

Reference yield: 63.0%

2-((2R,3R,11bS)-9-Benzyloxy-3-ethyl-10-methoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-yl)-N-[2-(5-benzyloxy-1H-indol-2-yl)-ethyl]-acetamide → (2R,3R,11bS)-9-Benzyloxy-2-(6-benzyloxy-4,9-dihydro-3H-β-carbolin-1-ylmethyl)-3-ethyl-10-methoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinoline (106550-20-3)

Guidance literature:

With trichlorophosphate; In toluene; for 2.5h; Heating;

Reference yield:

5-benzyloxytryptamine (20776-45-8) → (=/-)-9-benzyloxy-2β-<(6-benzyloxy-4,9-dihydro-3H-pyrido<3,4-b>indol-1-yl)methyl>-3α-ethyl-1,3,4,6,7,11bα-hexahydro-10-methoxy-2H-benzoquinolizine (74059-19-1,106550-20-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / diethyl phosphorocyanidate, Et₃N / dimethylformamide / 6 h / Ambient temperature

2: 69 percent / POCl₃ / toluene / 2.5 h / Heating

With diethyl cyanophosphonate; triethylamine; trichlorophosphate; In N,N-dimethyl-formamide; toluene;

DOI:10.1248/cpb.33.3724

upstream raw materials:

(+/-)-9-benzyloxy-N-<2-(5-benzyloxy-1H-indol-3-yl)ethyl>-3α-ethyl-1,3,4,6,7,11bα-hexahydro-10-methoxy-2H-benzoquinolizine-2β-acetamide

5-benzyloxytryptamine

(+/-)-9-benzyloxy-3α-ethyl-1,3,4,6,7,11bα-hexahydro-10-methoxy-2H-benzoquinolizine-2β-acetic acid

((3S,4S)-6-Ethoxy-3-ethyl-2,3,4,5-tetrahydro-pyridin-4-yl)-acetic acid ethyl ester

Downstream raw materials:

<2R^*-<2α(R^*),3β,11bβ>>-9-benzyloxy-2-<(6-benzyloxy-2,3,4,9-tetrahydro-1H-pyrido<3,4-b>indol-1-yl)methyl>-3-ethyl-1,3,4,6,7,11b-hexahydro-10-methoxy-2H-benzoquinolizine

<2R^*-<2α(S^*),3β,11bβ>>-9-benzyloxy-2-<(6-benzyloxy-2,3,4,9-tetrahydro-1H-pyrido<3,4-b>indol-1-yl)methyl>-3-ethyl-1,3,4,6,7,11b-hexahydro-10-methoxy-2H-benzoquinolizine

<2S-<2α(R*),3β,11bβ>>-9-benzyloxy-2-<(6-benzyloxy-2,3,4,9-tetrahydro-1H-pyrido<3,4-b>indol-1-yl)methyl>-3-ethyl-1,3,4,6,7,11b-hexahydro-10-methoxy-2H-benzoquinolizine

(+)-O,O-dibenzyl-9-demethyltubulosine