(1S,5R,6R,7R,8S)-7-benzyloxy-6,8-dimethyl-2,9-dioxabicyclo<3.3.1>nonan-3-one

Base Information

Chemical Name:(1S,5R,6R,7R,8S)-7-benzyloxy-6,8-dimethyl-2,9-dioxabicyclo<3.3.1>nonan-3-one
CAS No.:238757-57-8
Molecular Formula:C₁₆H₂₀O₄
Molecular Weight:276.332
Hs Code.:

Synonyms:(1S,5R,6R,7R,8S)-7-benzyloxy-6,8-dimethyl-2,9-dioxabicyclo<3.3.1>nonan-3-one

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Chemical Property of (1S,5R,6R,7R,8S)-7-benzyloxy-6,8-dimethyl-2,9-dioxabicyclo<3.3.1>nonan-3-one

Chemical Property:

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Technology Process of (1S,5R,6R,7R,8S)-7-benzyloxy-6,8-dimethyl-2,9-dioxabicyclo<3.3.1>nonan-3-one

There total 8 articles about (1S,5R,6R,7R,8S)-7-benzyloxy-6,8-dimethyl-2,9-dioxabicyclo<3.3.1>nonan-3-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:

: (1S,2R,3R,4S,5S)-3-Benzyloxy-2,4-dimethyl-8-oxa-bicyclo[3.2.1]octan-6-one

: 238757-54-5
(1S,5R,6S,7S,8S)-7-benzyloxy-6,8-dimethyl-2,9-dioxabicyclo<3.3.1>nonan-3-one

: 238757-57-8
(1S,5R,6R,7R,8S)-7-benzyloxy-6,8-dimethyl-2,9-dioxabicyclo<3.3.1>nonan-3-one

: 308350-13-2
(1R,5S,6S,7R,8R)-7-Benzyloxy-6,8-dimethyl-2,9-dioxa-bicyclo[3.3.1]nonan-3-one

Guidance literature:: With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20 ℃; for 15h;
DOI:10.1002/(SICI)1521-3765(20000915)6:18<3313::AID-CHEM3313>3.0.CO;2-0

Reference yield:

: C₁₆H₂₀O₂

: 238757-57-8
(1S,5R,6R,7R,8S)-7-benzyloxy-6,8-dimethyl-2,9-dioxabicyclo<3.3.1>nonan-3-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: (-)-(Ipc)2BH / tetrahydrofuran / 336 h / -15 °C

1.2: 98 percent / H₂O₂; NaOH / tetrahydrofuran / 3 h

2.1: 96 percent / PCC; SiO₂ / CH₂Cl₂ / 15 h / 20 °C

3.1: m-CPBA; NaHCO₃ / CH₂Cl₂ / 15 h / 20 °C

With silica gel; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; diisopinocampheylborane; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; 1.1: Addition / 1.2: Oxidation / 2.1: Oxidation / 3.1: Rearrangement;
DOI:10.1002/(SICI)1521-3765(20000915)6:18<3313::AID-CHEM3313>3.0.CO;2-0

Reference yield:

: 37081-60-0
trans-2,4-dimethyl-8-oxabicyclo<3.2.1>oct-6-en-3-one

: 238757-57-8
(1S,5R,6R,7R,8S)-7-benzyloxy-6,8-dimethyl-2,9-dioxabicyclo<3.3.1>nonan-3-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: 89 percent / DIBAH / tetrahydrofuran / 11 h / -78 °C

2.1: NaH / tetrahydrofuran

2.2: 99 percent / tetrahydrofuran / 16 h / Heating

3.1: (-)-(Ipc)2BH / tetrahydrofuran / 336 h / -15 °C

3.2: 98 percent / H₂O₂; NaOH / tetrahydrofuran / 3 h

4.1: 96 percent / PCC; SiO₂ / CH₂Cl₂ / 15 h / 20 °C

5.1: m-CPBA; NaHCO₃ / CH₂Cl₂ / 15 h / 20 °C

With silica gel; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; diisopinocampheylborane; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; 1.1: Reduction / 2.1: Metallation / 2.2: Etherification / 3.1: Addition / 3.2: Oxidation / 4.1: Oxidation / 5.1: Rearrangement;
DOI:10.1002/(SICI)1521-3765(20000915)6:18<3313::AID-CHEM3313>3.0.CO;2-0