(S)-4-Benzyloxy-1-((1R,3S,4S,7S,8R,9S)-7-isopropyl-1-methoxy-4-methyl-11-oxa-tricyclo[6.2.1.0^4,9]undec-3-yl)-3-methyl-butan-1-one

Base Information

• Chemical Name: (S)-4-Benzyloxy-1-((1R,3S,4S,7S,8R,9S)-7-isopropyl-1-methoxy-4-methyl-11-oxa-tricyclo[6.2.1.0^4,9]undec-3-yl)-3-methyl-butan-1-one
• CAS No.: 215227-89-7
• Molecular Formula: C₂₇H₄₀O₄
• Molecular Weight: 428.612

Synonyms:(S)-4-Benzyloxy-1-((1R,3S,4S,7S,8R,9S)-7-isopropyl-1-methoxy-4-methyl-11-oxa-tricyclo[6.2.1.0^4,9]undec-3-yl)-3-methyl-butan-1-one

Chemical Property of (S)-4-Benzyloxy-1-((1R,3S,4S,7S,8R,9S)-7-isopropyl-1-methoxy-4-methyl-11-oxa-tricyclo[6.2.1.0^4,9]undec-3-yl)-3-methyl-butan-1-one

Chemical Property:

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Technology Process of (S)-4-Benzyloxy-1-((1R,3S,4S,7S,8R,9S)-7-isopropyl-1-methoxy-4-methyl-11-oxa-tricyclo[6.2.1.0^4,9]undec-3-yl)-3-methyl-butan-1-one

There total 1 articles about (S)-4-Benzyloxy-1-((1R,3S,4S,7S,8R,9S)-7-isopropyl-1-methoxy-4-methyl-11-oxa-tricyclo[6.2.1.0^4,9]undec-3-yl)-3-methyl-butan-1-one 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%

(4S,4aS,7S,8R,8aS)-4-((S)-4-Benzyloxy-3-methyl-butyryl)-8-hydroxy-7-isopropyl-4a-methyl-octahydro-naphthalen-2-one (160715-33-3) + trimethyl orthoformate (149-73-5) → (S)-4-Benzyloxy-1-((1R,3S,4S,7S,8R,9S)-7-isopropyl-1-methoxy-4-methyl-11-oxa-tricyclo[6.2.1.04,9]undec-3-yl)-3-methyl-butan-1-one (215227-89-7)

Guidance literature:

With acid; In methanol; for 4h; Ambient temperature;

DOI:10.1002/(SICI)1521-3773(19980904)37:16<2226::AID-ANIE2226>3.0.CO;2-H

Reference yield: 92.0%

(S)-4-Benzyloxy-1-((1R,3S,4S,7S,8R,9S)-7-isopropyl-1-methoxy-4-methyl-11-oxa-tricyclo[6.2.1.04,9]undec-3-yl)-3-methyl-butan-1-one (215227-89-7) → (S)-4-Benzyloxy-1-((1S,3S,4R,7S,8R,9S)-7-isopropyl-1-methoxy-4-methyl-11-oxa-tricyclo[6.2.1.04,9]undec-3-yl)-3-methyl-butan-1-ol

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; 1.) 0 deg C to r.t., 2.) r.t. 4 h;

DOI:10.1002/(SICI)1521-3773(19980904)37:16<2226::AID-ANIE2226>3.0.CO;2-H

Reference yield:

(S)-4-Benzyloxy-1-((1R,3S,4S,7S,8R,9S)-7-isopropyl-1-methoxy-4-methyl-11-oxa-tricyclo[6.2.1.04,9]undec-3-yl)-3-methyl-butan-1-one (215227-89-7) → (1S,3S,4R,7S,8R,9S)-3-((S)-4-Benzyloxy-3-methyl-butyl)-7-isopropyl-1-methoxy-4-methyl-11-oxa-tricyclo[6.2.1.04,9]undecane (215227-95-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 92 percent / LiAlH₄ / diethyl ether / 1.) 0 deg C to r.t., 2.) r.t. 4 h

2: 97 percent / pyridine, DMAP / 3 h / 30 °C

3: 75 percent / Bu₃SnH, AIBN / toluene / 8 h / Heating

With pyridine; dmap; lithium aluminium tetrahydride; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In diethyl ether; toluene;

DOI:10.1002/(SICI)1521-3773(19980904)37:16<2226::AID-ANIE2226>3.0.CO;2-H

upstream raw materials:

(4S,4aS,7S,8R,8aS)-4-((S)-4-Benzyloxy-3-methyl-butyryl)-8-hydroxy-7-isopropyl-4a-methyl-octahydro-naphthalen-2-one

trimethyl orthoformate

Downstream raw materials:

(1S,3S,4R,7S,8R,9S)-3-((S)-4-Benzyloxy-3-methyl-butyl)-7-isopropyl-1-methoxy-4-methyl-11-oxa-tricyclo[6.2.1.0^4,9]undecane

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