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

Base Information

• Chemical Name: (1S,3S,4S,6R,7S,8R)-3,4-diphenyl-2,5-dioxabicyclo[4,4,0]dec-9-ene-7,8-diol
• CAS No.: 215026-33-8
• Molecular Formula: C₂₀H₂₀O₄
• Molecular Weight: 324.376
• Mol file: 215026-33-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 17 articles about (1S,3S,4S,6R,7S,8R)-3,4-diphenyl-2,5-dioxabicyclo[4,4,0]dec-9-ene-7,8-diol 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: 92.0%

(1S,3S,4S,6S,7S,8R)-3,4-diphenyl-2,5-dioxa-7-tert-butyldiphenylsilyloxybicyclo[4,4,0]dec-9-en-8-ol (849596-47-0) → (1S,3S,4S,6R,7S,8R)-3,4-diphenyl-2,5-dioxabicyclo[4,4,0]dec-9-ene-7,8-diol (215026-33-8)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 5h; Ambient temperature;

DOI:10.1039/a804072i

Reference yield:

(1S,3S,4S,6S,7S,8S,9S)-3,4-diphenyl-2,5-dioxa-7-tert-butyldiphenylsilyloxy-9-phenylselenobicyclo[4,4,0]decan-8-ol (849596-45-8) → (1S,3S,4S,6R,7S,8R)-3,4-diphenyl-2,5-dioxabicyclo[4,4,0]dec-9-ene-7,8-diol (215026-33-8)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 92 percent / tetrabutylammonium fluoride / tetrahydrofuran / 5 h / 20 °C

With sodium periodate; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; In tetrahydrofuran; methanol; water;

DOI:10.1016/j.tet.2005.01.003

Reference yield:

(1S,3S,4S,6S,7S,8S)-3,4-diphenyl-2,5-dioxa-7,8-epoxybicyclo[4,4,0]decane (215026-22-5) → (1S,3S,4S,6R,7S,8R)-3,4-diphenyl-2,5-dioxabicyclo[4,4,0]dec-9-ene-7,8-diol (215026-33-8)

Guidance literature:

Multi-step reaction with 7 steps

1: NaBH₄ / ethanol / 4 h / Heating

2: 97 mg / H₂O₂ / ethanol; tetrahydrofuran / Heating

3: 87 percent / imidazole / dimethylformamide / 14 h / 80 °C

4: 51 percent / mCPBA; NaHCO₃ / CH₂Cl₂ / 20 h / Heating

5: 83 percent / NaBH₄ / butan-1-ol / 24 h / Heating

6: 90 percent / NaIO₄; NaHCO₃ / methanol; H₂O / 48 h / 90 °C

7: 92 percent / tetrabutylammonium fluoride / tetrahydrofuran / 5 h / 20 °C

With 1H-imidazole; sodium tetrahydroborate; sodium periodate; tetrabutyl ammonium fluoride; dihydrogen peroxide; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; butan-1-ol;

DOI:10.1016/j.tet.2005.01.003

upstream raw materials:

(1S,3S,4S,6S,7S,8R)-3,4-diphenyl-2,5-dioxa-7-tert-butyldiphenylsilyloxybicyclo[4,4,0]dec-9-en-8-ol

(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

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