(-)-(1S,5S,6S,8R,9R)-9-benzyloxy-5-hydroxy-8-phenyl-2,7-dioxabicyclo[4.3.0]nonan-3-one

Base Information

Chemical Name:(-)-(1S,5S,6S,8R,9R)-9-benzyloxy-5-hydroxy-8-phenyl-2,7-dioxabicyclo[4.3.0]nonan-3-one
CAS No.:181781-56-6
Molecular Formula:C₂₀H₂₀O₅
Molecular Weight:340.376
Hs Code.:

Synonyms:(-)-(1S,5S,6S,8R,9R)-9-benzyloxy-5-hydroxy-8-phenyl-2,7-dioxabicyclo[4.3.0]nonan-3-one

Suppliers and Price of (-)-(1S,5S,6S,8R,9R)-9-benzyloxy-5-hydroxy-8-phenyl-2,7-dioxabicyclo[4.3.0]nonan-3-one

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Total 0 raw suppliers

Chemical Property of (-)-(1S,5S,6S,8R,9R)-9-benzyloxy-5-hydroxy-8-phenyl-2,7-dioxabicyclo[4.3.0]nonan-3-one

Chemical Property:

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Technology Process of (-)-(1S,5S,6S,8R,9R)-9-benzyloxy-5-hydroxy-8-phenyl-2,7-dioxabicyclo[4.3.0]nonan-3-one

There total 15 articles about (-)-(1S,5S,6S,8R,9R)-9-benzyloxy-5-hydroxy-8-phenyl-2,7-dioxabicyclo[4.3.0]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:

: 153000-32-9
(R)-5-[(1R,2S,3R)-2-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-3-phenyl-propyl]-5H-furan-2-one

: 181781-56-6
(-)-(1S,5S,6S,8R,9R)-9-benzyloxy-5-hydroxy-8-phenyl-2,7-dioxabicyclo[4.3.0]nonan-3-one

Guidance literature:: Multi-step reaction with 12 steps

1: 97 percent / CH₂Cl₂ / 10 h / Ambient temperature

2: DIBALH / diethyl ether / 0.17 h / -78 °C

4: 96 percent / DMAP / CH₂Cl₂ / 1.5 h

5: 89 percent / TBAF-HF / tetrahydrofuran

6: 75 percent / OsO₄, NMO / acetone; H₂O / 1.5 h / Ambient temperature

7: 62 percent / SmI₂ / tetrahydrofuran; ethane-1,2-diol / 10 h / Ambient temperature

8: DIBALH / diethyl ether / 0.17 h / -78 °C

9: 32.6 mg / p-TsOH*H₂O / 15 h / Ambient temperature

10: TPAP, NMO, 4A MS / acetonitrile / 0.5 h / Ambient temperature

11: LiAlH₄ / tetrahydrofuran / 0.33 h / -20 °C

12: m-CPBA, BF₃*Et₂O / CH₂Cl₂ / 1.5 h / Ambient temperature

With dmap; osmium(VIII) oxide; lithium aluminium tetrahydride; N-methyl-2-indolinone; samarium diiodide; tetrapropylammonium perruthennate; boron trifluoride diethyl etherate; hydrogen fluoride; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; diethyl ether; dichloromethane; water; ethylene glycol; acetone; acetonitrile;
DOI:10.1021/jo970725u

Reference yield:

: 181534-69-0
(2R,3R,3aR,7aS)-3-(benzyloxy)-2-phenyl-3,3a-dihydro-2H-furo[3,2-b]pyran-5(7aH)-one

: 181781-56-6
(-)-(1S,5S,6S,8R,9R)-9-benzyloxy-5-hydroxy-8-phenyl-2,7-dioxabicyclo[4.3.0]nonan-3-one

Guidance literature:: Multi-step reaction with 7 steps

1: 75 percent / OsO₄, NMO / acetone; H₂O / 1.5 h / Ambient temperature

2: 62 percent / SmI₂ / tetrahydrofuran; ethane-1,2-diol / 10 h / Ambient temperature

3: DIBALH / diethyl ether / 0.17 h / -78 °C

4: 32.6 mg / p-TsOH*H₂O / 15 h / Ambient temperature

5: TPAP, NMO, 4A MS / acetonitrile / 0.5 h / Ambient temperature

6: LiAlH₄ / tetrahydrofuran / 0.33 h / -20 °C

7: m-CPBA, BF₃*Et₂O / CH₂Cl₂ / 1.5 h / Ambient temperature

With osmium(VIII) oxide; lithium aluminium tetrahydride; N-methyl-2-indolinone; samarium diiodide; tetrapropylammonium perruthennate; boron trifluoride diethyl etherate; diisobutylaluminium hydride; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; diethyl ether; dichloromethane; water; ethylene glycol; acetone; acetonitrile;
DOI:10.1021/jo970725u

Reference yield:

: (2R,3R,3aS,7aR)-3-Benzyloxy-5-methoxy-2-phenyl-hexahydro-furo[3,2-b]pyran-7-one

: 181781-56-6
(-)-(1S,5S,6S,8R,9R)-9-benzyloxy-5-hydroxy-8-phenyl-2,7-dioxabicyclo[4.3.0]nonan-3-one

Guidance literature:: Multi-step reaction with 2 steps

1: LiAlH₄ / tetrahydrofuran / 0.33 h / -20 °C

2: m-CPBA, BF₃*Et₂O / CH₂Cl₂ / 1.5 h / Ambient temperature

With lithium aluminium tetrahydride; boron trifluoride diethyl etherate; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo970725u