(R)-1-Benzyloxy-2-((2R,4aR,7R,8aR)-4,4,7-trimethyl-hexahydro-1-oxa-3-thia-naphthalen-2-yl)-propan-2-ol

Base Information

Chemical Name:(R)-1-Benzyloxy-2-((2R,4aR,7R,8aR)-4,4,7-trimethyl-hexahydro-1-oxa-3-thia-naphthalen-2-yl)-propan-2-ol
CAS No.:112066-93-0
Molecular Formula:C₂₁H₃₂O₃S
Molecular Weight:364.549
Hs Code.:

Synonyms:(R)-1-Benzyloxy-2-((2R,4aR,7R,8aR)-4,4,7-trimethyl-hexahydro-1-oxa-3-thia-naphthalen-2-yl)-propan-2-ol

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Chemical Property of (R)-1-Benzyloxy-2-((2R,4aR,7R,8aR)-4,4,7-trimethyl-hexahydro-1-oxa-3-thia-naphthalen-2-yl)-propan-2-ol

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Technology Process of (R)-1-Benzyloxy-2-((2R,4aR,7R,8aR)-4,4,7-trimethyl-hexahydro-1-oxa-3-thia-naphthalen-2-yl)-propan-2-ol

There total 4 articles about (R)-1-Benzyloxy-2-((2R,4aR,7R,8aR)-4,4,7-trimethyl-hexahydro-1-oxa-3-thia-naphthalen-2-yl)-propan-2-ol 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:

: 75-16-1
methylmagnesium bromide

: 107288-57-3
2-Benzyloxy-1-((2R,4aR,7R,8aR)-4,4,7-trimethyl-hexahydro-1-oxa-3-thia-naphthalen-2-yl)-ethanone

: 112066-93-0
(R)-1-Benzyloxy-2-((2R,4aR,7R,8aR)-4,4,7-trimethyl-hexahydro-1-oxa-3-thia-naphthalen-2-yl)-propan-2-ol

: 107288-63-1
(S)-1-Benzyloxy-2-((2R,4aR,7R,8aR)-4,4,7-trimethyl-hexahydro-1-oxa-3-thia-naphthalen-2-yl)-propan-2-ol

Guidance literature:: In tetrahydrofuran; at -78 ℃; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
DOI:10.1016/S0040-4039(00)84759-0

Reference yield:

: 60656-87-3
benzyloxyacetoaldehyde

: 112066-93-0
(R)-1-Benzyloxy-2-((2R,4aR,7R,8aR)-4,4,7-trimethyl-hexahydro-1-oxa-3-thia-naphthalen-2-yl)-propan-2-ol

Guidance literature:: Multi-step reaction with 3 steps

1: 43 percent / 1) 1.5M n-BuLi / tetrahydrofuran; hexane / 1)-78 deg C, 3 min then 0 deg C; 2) -78 deg C, 3 h then -25 deg C, overnight

2: 1) Me₂SO, trifluoroacetic anhydride; 2) triethylamine / 1) CH₂Cl₂, -78 deg C, 2 h; 2) CH₂Cl₂, 0 deg C

3: diethyl ether; tetrahydrofuran / 4 h / -78 °C

With n-butyllithium; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; In tetrahydrofuran; diethyl ether; hexane;
DOI:10.1021/ja00210a028

Reference yield:

: 79618-03-4
(4aR,7R,8aR)-4,4,7-Trimethyl-hexahydro-1-oxa-3-thia-naphthalene

: 112066-93-0
(R)-1-Benzyloxy-2-((2R,4aR,7R,8aR)-4,4,7-trimethyl-hexahydro-1-oxa-3-thia-naphthalen-2-yl)-propan-2-ol

Guidance literature:: Multi-step reaction with 3 steps

1: 43 percent / 1) 1.5M n-BuLi / tetrahydrofuran; hexane / 1)-78 deg C, 3 min then 0 deg C; 2) -78 deg C, 3 h then -25 deg C, overnight

2: 1) Me₂SO, trifluoroacetic anhydride; 2) triethylamine / 1) CH₂Cl₂, -78 deg C, 2 h; 2) CH₂Cl₂, 0 deg C

3: diethyl ether; tetrahydrofuran / 4 h / -78 °C

With n-butyllithium; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; In tetrahydrofuran; diethyl ether; hexane;
DOI:10.1021/ja00210a028