(1S,3S,4S,6R,7S,8R,9R,10R)-3,4-diphenyl-2,5-dioxabicyclo-[4,4,0]decane-7,8,9,10-tetrol

Base Information

• Chemical Name: (1S,3S,4S,6R,7S,8R,9R,10R)-3,4-diphenyl-2,5-dioxabicyclo-[4,4,0]decane-7,8,9,10-tetrol
• CAS No.: 215026-34-9
• Molecular Formula: C₂₀H₂₂O₆
• Molecular Weight: 358.391
• Mol file: 215026-34-9.mol

Synonyms:(1S,3S,4S,6R,7S,8R,9R,10R)-3,4-diphenyl-2,5-dioxabicyclo-[4,4,0]decane-7,8,9,10-tetrol

Chemical Property of (1S,3S,4S,6R,7S,8R,9R,10R)-3,4-diphenyl-2,5-dioxabicyclo-[4,4,0]decane-7,8,9,10-tetrol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,3S,4S,6R,7S,8R,9R,10R)-3,4-diphenyl-2,5-dioxabicyclo-[4,4,0]decane-7,8,9,10-tetrol

There total 17 articles about (1S,3S,4S,6R,7S,8R,9R,10R)-3,4-diphenyl-2,5-dioxabicyclo-[4,4,0]decane-7,8,9,10-tetrol 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: 87.0%

(1S,3S,4S,6R,7S,8R)-3,4-diphenyl-2,5-dioxabicyclo[4,4,0]dec-9-ene-7,8-diol (215026-33-8) → (1S,3S,4S,6R,7S,8R,9R,10R)-3,4-diphenyl-2,5-dioxabicyclo-[4,4,0]decane-7,8,9,10-tetrol (215026-34-9)

Guidance literature:

With potassium osmate(VI); N-methyl-2-indolinone; water; In acetone; for 18h; Heating;

DOI:10.1039/a804072i

Reference yield:

(1S,3S,4S,6S,7S)-3,4-diphenyl-7-phenylseleno-2,5-dioxabicyclo[4,4,0]decane (215026-15-6) → (1S,3S,4S,6R,7S,8R,9R,10R)-3,4-diphenyl-2,5-dioxabicyclo-[4,4,0]decane-7,8,9,10-tetrol (215026-34-9)

Guidance literature:

Multi-step reaction with 10 steps

1: 90 percent / NaIO₄; NaHCO₃ / methanol; H₂O / 48 h / 90 °C

2: 89 percent / dimethyldioxirane / acetone / 3 h / 0 °C

3: NaBH₄ / ethanol / 4 h / Heating

4: 97 mg / H₂O₂ / ethanol; tetrahydrofuran / Heating

5: 87 percent / imidazole / dimethylformamide / 14 h / 80 °C

6: 51 percent / mCPBA; NaHCO₃ / CH₂Cl₂ / 20 h / Heating

7: 83 percent / NaBH₄ / butan-1-ol / 24 h / Heating

8: 90 percent / NaIO₄; NaHCO₃ / methanol; H₂O / 48 h / 90 °C

9: 92 percent / tetrabutylammonium fluoride / tetrahydrofuran / 5 h / 20 °C

10: 87 percent / N-methylmorpholine N-oxide; K₂OsO₄ / acetone; H₂O / 20 h / Heating

With 1H-imidazole; sodium tetrahydroborate; potassium osmate(VI); sodium periodate; tetrabutyl ammonium fluoride; dihydrogen peroxide; 3,3-dimethyldioxirane; sodium hydrogencarbonate; 4-methylmorpholine N-oxide; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; butan-1-ol;

DOI:10.1016/j.tet.2005.01.003

Reference yield:

(1S,3S,4S,6S,7S)-3,4-diphenyl-2,5-dioxa-7-tert-butyldiphenylsilyloxybicyclo[4,4,0]dec-8-ene (215026-27-0) → (1S,3S,4S,6R,7S,8R,9R,10R)-3,4-diphenyl-2,5-dioxabicyclo-[4,4,0]decane-7,8,9,10-tetrol (215026-34-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 51 percent / mCPBA; NaHCO₃ / CH₂Cl₂ / 20 h / Heating

2: 83 percent / NaBH₄ / butan-1-ol / 24 h / Heating

3: 90 percent / NaIO₄; NaHCO₃ / methanol; H₂O / 48 h / 90 °C

4: 92 percent / tetrabutylammonium fluoride / tetrahydrofuran / 5 h / 20 °C

5: 87 percent / N-methylmorpholine N-oxide; K₂OsO₄ / acetone; H₂O / 20 h / Heating

With sodium tetrahydroborate; potassium osmate(VI); sodium periodate; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; 4-methylmorpholine N-oxide; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane; water; acetone; butan-1-ol;

DOI:10.1016/j.tet.2005.01.003

upstream raw materials:

(1S,3S,4S,6R,7S,8R)-3,4-diphenyl-2,5-dioxabicyclo[4,4,0]dec-9-ene-7,8-diol

(S,S)-hydrobenzoin

rac-3-bromocyclohexene

(1S,3S,4S,6R)-3,4-diphenyl-2,5-dioxabicyclo[4,4,0]dec-7-ene

Downstream raw materials:

D-chiro-inositol