(+)-6-chloro-2,2-dimethyl-5-(phenylselenyl)tetrahydrocyclopenta[1,3]dioxol-4-ol

Base Information

• Chemical Name: (+)-6-chloro-2,2-dimethyl-5-(phenylselenyl)tetrahydrocyclopenta[1,3]dioxol-4-ol
• CAS No.: 910138-75-9
• Molecular Formula: C₁₄H₁₇ClO₃Se
• Molecular Weight: 347.7
• Mol file: 910138-75-9.mol

Synonyms:(+)-6-chloro-2,2-dimethyl-5-(phenylselenyl)tetrahydrocyclopenta[1,3]dioxol-4-ol

Chemical Property of (+)-6-chloro-2,2-dimethyl-5-(phenylselenyl)tetrahydrocyclopenta[1,3]dioxol-4-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-6-chloro-2,2-dimethyl-5-(phenylselenyl)tetrahydrocyclopenta[1,3]dioxol-4-ol

There total 1 articles about (+)-6-chloro-2,2-dimethyl-5-(phenylselenyl)tetrahydrocyclopenta[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: 73.0%

Phenylselenyl chloride (5707-04-0) + (3aS,6aS)-2,2-dimethyl-3a,6a-dihydro-4H-cyclopenta[d][1,3]dioxol-4-one (104010-72-2) → (+)-6-chloro-2,2-dimethyl-5-(phenylselenyl)tetrahydrocyclopenta[1,3]dioxol-4-ol (910138-75-9)

Guidance literature:

(3aS,6aS)-2,2-dimethyl-3a,6a-dihydro-4H-cyclopenta[d][1,3]dioxol-4-one; With methanol; sodium tetrahydroborate; cerium(III) chloride; at 23 ℃;

Phenylselenyl chloride; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1021/ja063304f

Reference yield:

(+)-6-chloro-2,2-dimethyl-5-(phenylselenyl)tetrahydrocyclopenta[1,3]dioxol-4-ol (910138-75-9) → C25H23NO6 (910138-89-5)

Guidance literature:

Multi-step reaction with 12 steps

1.1: m-CPBA / CH₂Cl₂ / 0.25 h / 23 °C

1.2: 91 percent / triethylamine / CH₂Cl₂ / 17 h / 40 °C

2.1: 98 percent / Dess-Martin periodane / CH₂Cl₂ / 2 h / 23 °C

3.1: 85 percent / triethylamine / tetrahydrofuran / 3 h / 25 °C

4.1: 76 percent / Cs₂CO₃ / dioxane / 18 h / Heating

5.1: 75 percent / Cs₂CO₃ / acetonitrile / 20 h / 25 °C

6.1: AgOTf / CH₂Cl₂ / 1 h / 25 °C

6.2: 77 percent / TBAT / CH₂Cl₂ / 20 h / -45 - 25 °C

7.1: 74 percent / samarium diiodide; HMPA / 2-methyl-propan-2-ol / 3 h / -78 - -45 °C

8.1: 99 percent / Schwartz's reagent / tetrahydrofuran / 16 h / Heating

9.1: 86 percent / KHMDS / tetrahydrofuran / 1 h / 0 °C

10.1: 99 percent / HCl; methanol / 16 h / 25 °C

11.1: Yb(OTf)3*xH₂O / CH₂Cl₂ / 48 h / 0 °C

11.2: 50 percent / ortho-iodoxybenzoic acid / dimethylsulfoxide / 20 h / 25 °C

12.1: 42 percent / chromium(II) chloride / acetone; H₂O / 1 h / 25 °C

With chromium dichloride; hydrogenchloride; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; samarium diiodide; Schwartz's reagent; silver trifluoromethanesulfonate; potassium hexamethylsilazane; caesium carbonate; Dess-Martin periodane; triethylamine; 3-chloro-benzenecarboperoxoic acid; ytterbium(III) triflate; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; acetone; acetonitrile; tert-butyl alcohol;

DOI:10.1021/ja063304f

Reference yield:

(+)-6-chloro-2,2-dimethyl-5-(phenylselenyl)tetrahydrocyclopenta[1,3]dioxol-4-ol (910138-75-9) → C28H29NO7 (910138-85-1)

Guidance literature:

Multi-step reaction with 9 steps

1.1: m-CPBA / CH₂Cl₂ / 0.25 h / 23 °C

1.2: 91 percent / triethylamine / CH₂Cl₂ / 17 h / 40 °C

2.1: 98 percent / Dess-Martin periodane / CH₂Cl₂ / 2 h / 23 °C

3.1: 85 percent / triethylamine / tetrahydrofuran / 3 h / 25 °C

4.1: 76 percent / Cs₂CO₃ / dioxane / 18 h / Heating

5.1: 75 percent / Cs₂CO₃ / acetonitrile / 20 h / 25 °C

6.1: AgOTf / CH₂Cl₂ / 1 h / 25 °C

6.2: 77 percent / TBAT / CH₂Cl₂ / 20 h / -45 - 25 °C

7.1: 74 percent / samarium diiodide; HMPA / 2-methyl-propan-2-ol / 3 h / -78 - -45 °C

8.1: 99 percent / Schwartz's reagent / tetrahydrofuran / 16 h / Heating

9.1: 86 percent / KHMDS / tetrahydrofuran / 1 h / 0 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; samarium diiodide; Schwartz's reagent; silver trifluoromethanesulfonate; potassium hexamethylsilazane; caesium carbonate; Dess-Martin periodane; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; 1,4-dioxane; dichloromethane; acetonitrile; tert-butyl alcohol;

DOI:10.1021/ja063304f

upstream raw materials:

Phenylselenyl chloride

(3aS,6aS)-2,2-dimethyl-3a,6a-dihydro-4H-cyclopenta[d][1,3]dioxol-4-one

Downstream raw materials:

C₂₅H₂₃NO₆

C₂₈H₂₉NO₇

C₂₅H₂₅NO₇

C₃₁H₃₅NO₈S