Toluene-4-sulfonic acid (E)-(3R,6R)-6-((1aR,3aR,3bS,5aR,6R,8aS,8bS,10R,10aR)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-2,3-dimethyl-hept-4-enyl ester

Base Information

Chemical Name:Toluene-4-sulfonic acid (E)-(3R,6R)-6-((1aR,3aR,3bS,5aR,6R,8aS,8bS,10R,10aR)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-2,3-dimethyl-hept-4-enyl ester
CAS No.:137435-98-4
Molecular Formula:C₃₆H₅₄O₄S
Molecular Weight:582.888
Hs Code.:

Toluene-4-sulfonic acid (E)-(3R,6R)-6-((1aR,3aR,3bS,5aR,6R,8aS,8bS,10R,10aR)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-2,3-dimethyl-hept-4-enyl ester

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Chemical Property of Toluene-4-sulfonic acid (E)-(3R,6R)-6-((1aR,3aR,3bS,5aR,6R,8aS,8bS,10R,10aR)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-2,3-dimethyl-hept-4-enyl ester

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Technology Process of Toluene-4-sulfonic acid (E)-(3R,6R)-6-((1aR,3aR,3bS,5aR,6R,8aS,8bS,10R,10aR)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-2,3-dimethyl-hept-4-enyl ester

There total 8 articles about Toluene-4-sulfonic acid (E)-(3R,6R)-6-((1aR,3aR,3bS,5aR,6R,8aS,8bS,10R,10aR)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-2,3-dimethyl-hept-4-enyl 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: 90.0%

: 189013-48-7
(22E)-6β-methoxy-3α,5-cyclo-24-α-methyl-5α-cholest-22-en-26-ol

: 98-59-9
p-toluenesulfonyl chloride

: 137435-98-4,137435-99-5,137492-93-4,137492-94-5
Toluene-4-sulfonic acid (E)-(3R,6R)-6-((1aR,3aR,3bS,5aR,6R,8aS,8bS,10R,10aR)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-2,3-dimethyl-hept-4-enyl ester

Guidance literature:: With pyridine;

Reference yield: 76.0%

: 96572-94-0,133164-27-9,133164-28-0,133164-29-1,133164-30-4
(E)-(3S,6R)-6-((1aR,3aR,3bS,5aR,6R,8aS,8bS,10R,10aR)-10-Methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-2,3-dimethyl-hept-4-en-1-ol

: 98-59-9
p-toluenesulfonyl chloride

: 137435-98-4,137435-99-5,137492-93-4,137492-94-5
Toluene-4-sulfonic acid (E)-(3S,6R)-6-((1aR,3aR,3bS,5aR,6R,8aS,8bS,10R,10aR)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-2,3-dimethyl-hept-4-enyl ester

Guidance literature:: With pyridine;

Reference yield:

: 25819-77-6
(20S)-6β-methoxy-3α,5-cyclo-5α-pregnane-20-carbaldehyde

: 137435-98-4,137435-99-5,137492-93-4,137492-94-5
Toluene-4-sulfonic acid (E)-(3R,6R)-6-((1aR,3aR,3bS,5aR,6R,8aS,8bS,10R,10aR)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-2,3-dimethyl-hept-4-enyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 28 percent / BuLi / tetrahydrofuran / 3.42 h / -65 - -20 °C

2: 100 percent / Li / 2-methyl-propan-2-ol; liquid ammonia / 6 h / -50 °C

3: 82 percent / propionic acid / benzene / 0.75 h / Heating

4: 92 percent / LiAlH₄ / diethyl ether / 0.25 h

5: Et₃N / CH₂Cl₂ / 0.75 h / 0 °C

With lithium aluminium tetrahydride; n-butyllithium; lithium; propionic acid; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; ammonia; tert-butyl alcohol; benzene; 3: Claisen rearrangement;
DOI:10.1016/S0039-128X(02)00007-7