(3aS,4S,5R,7aR)-6-Benzenesulfonyl-5-[(tert-butyl-dimethyl-silanyl)-ethynyl]-2,2-dimethyl-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-4-ol

Base Information

• Chemical Name: (3aS,4S,5R,7aR)-6-Benzenesulfonyl-5-[(tert-butyl-dimethyl-silanyl)-ethynyl]-2,2-dimethyl-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-4-ol
• CAS No.: 205743-79-9
• Molecular Formula: C₂₃H₃₂O₅SSi
• Molecular Weight: 448.656
• Mol file: 205743-79-9.mol

Synonyms:(3aS,4S,5R,7aR)-6-Benzenesulfonyl-5-[(tert-butyl-dimethyl-silanyl)-ethynyl]-2,2-dimethyl-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-4-ol

Chemical Property of (3aS,4S,5R,7aR)-6-Benzenesulfonyl-5-[(tert-butyl-dimethyl-silanyl)-ethynyl]-2,2-dimethyl-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-4-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aS,4S,5R,7aR)-6-Benzenesulfonyl-5-[(tert-butyl-dimethyl-silanyl)-ethynyl]-2,2-dimethyl-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-4-ol

There total 10 articles about (3aS,4S,5R,7aR)-6-Benzenesulfonyl-5-[(tert-butyl-dimethyl-silanyl)-ethynyl]-2,2-dimethyl-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-4-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: 62.0%

(tert-butyldimethylsilyl)acetylene (86318-61-8) + 5,6-exo-(isopropylidenedioxy)-2-phenylsulfonyl-7-oxabicyclo[2.2.1]hept-2-ene (214278-38-3) → (3aS,4S,5R,7aR)-6-Benzenesulfonyl-5-[(tert-butyl-dimethyl-silanyl)-ethynyl]-2,2-dimethyl-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-4-ol (205743-79-9)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; toluene; at 0 ℃;

DOI:10.1016/S0040-4039(98)01414-2

Reference yield: 62.0%

LiCCSi(CH3)2(C(CH3)3) + 5,6-exo-(isopropylidenedioxy)-2-phenylsulfonyl-7-oxabicyclo[2.2.1]hept-2-ene (214278-38-3) → (3aS,4S,5R,7aR)-6-Benzenesulfonyl-5-[(tert-butyl-dimethyl-silanyl)-ethynyl]-2,2-dimethyl-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-4-ol (205743-79-9)

Guidance literature:

In toluene; at 0 ℃;

DOI:10.1016/S0040-4039(98)00109-9

Reference yield:

(+/-)-trans-2,3-bis(phenylsulfonyl)-7-oxabicyclo[2.2.1]hept-5-ene (87057-40-7) → (3aS,4S,5R,7aR)-6-Benzenesulfonyl-5-[(tert-butyl-dimethyl-silanyl)-ethynyl]-2,2-dimethyl-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-4-ol (205743-79-9)

Guidance literature:

Multi-step reaction with 9 steps

1: KOH / acetonitrile

2: OsO₄, Me₃NO*2H₂O / acetone; H₂O

3: NaH, TBAI / 24 h / 0 °C

4: DDQ / CH₂Cl₂; H₂O / 24 h

5: Et₃N / CH₂Cl₂

6: BF₃*OEt₂, EtSH

7: p-TsOH / acetone

8: 71 percent / K₂CO₃ / tetrahydrofuran; H₂O

9: 62 percent / n-BuLi / tetrahydrofuran; toluene / 0 °C

With potassium hydroxide; osmium(VIII) oxide; n-butyllithium; trimethylamine-N-oxide; boron trifluoride diethyl etherate; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; ethanethiol; In tetrahydrofuran; dichloromethane; water; acetone; toluene; acetonitrile;

DOI:10.1016/S0040-4039(98)01414-2

upstream raw materials:

5,6-exo-(isopropylidenedioxy)-2-phenylsulfonyl-7-oxabicyclo[2.2.1]hept-2-ene

(tert-butyldimethylsilyl)acetylene

(+/-)-trans-2,3-bis(phenylsulfonyl)-7-oxabicyclo[2.2.1]hept-5-ene

Downstream raw materials:

(3aS,4S,7aR)-6-Benzenesulfonyl-5-[(tert-butyl-dimethyl-silanyl)-ethynyl]-2,2-dimethyl-3a,4,7,7a-tetrahydro-benzo[1,3]dioxol-4-ol