(3R,5S)-5-[(S)-2,2,3,3,10,10-hexamethyl-9,9-diphenyl-4,8-dioxa-3,9-disilaundecan-5-yl]-3-methyldihydrofuran-2(3H)-one

Base Information

• Chemical Name: (3R,5S)-5-[(S)-2,2,3,3,10,10-hexamethyl-9,9-diphenyl-4,8-dioxa-3,9-disilaundecan-5-yl]-3-methyldihydrofuran-2(3H)-one
• CAS No.: 1015071-58-5
• Molecular Formula: C₃₀H₄₆O₄Si₂
• Molecular Weight: 526.864
• Mol file: 1015071-58-5.mol

Synonyms:(3R,5S)-5-[(S)-2,2,3,3,10,10-hexamethyl-9,9-diphenyl-4,8-dioxa-3,9-disilaundecan-5-yl]-3-methyldihydrofuran-2(3H)-one

Chemical Property of (3R,5S)-5-[(S)-2,2,3,3,10,10-hexamethyl-9,9-diphenyl-4,8-dioxa-3,9-disilaundecan-5-yl]-3-methyldihydrofuran-2(3H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,5S)-5-[(S)-2,2,3,3,10,10-hexamethyl-9,9-diphenyl-4,8-dioxa-3,9-disilaundecan-5-yl]-3-methyldihydrofuran-2(3H)-one

There total 7 articles about (3R,5S)-5-[(S)-2,2,3,3,10,10-hexamethyl-9,9-diphenyl-4,8-dioxa-3,9-disilaundecan-5-yl]-3-methyldihydrofuran-2(3H)-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: 85.0%

(S)-5-[(S)-3-(tert-butyldiphenylsilyloxy)-1-hydroxypropyl]dihydrofuran-2(3H)-one (1431372-83-6) + methyl iodide (74-88-4) → (3R,5S)-5-[(S)-2,2,3,3,10,10-hexamethyl-9,9-diphenyl-4,8-dioxa-3,9-disilaundecan-5-yl]-3-methyldihydrofuran-2(3H)-one (1015071-58-5)

Guidance literature:

(S)-5-[(S)-3-(tert-butyldiphenylsilyloxy)-1-hydroxypropyl]dihydrofuran-2(3H)-one; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 1h;

methyl iodide; In tetrahydrofuran; at -78 ℃; for 1h; stereoselective reaction;

DOI:10.1055/s-0032-1318141

Reference yield:

(3R,5S)-5-[(S)-3-(tert-butyldiphenylsilanyloxy)-1-hydroxy-propyl]-3-methyl-dihydro-furan-2-one + tert-butyldimethylsilyl chloride (18162-48-6) → (3R,5S)-5-[(S)-2,2,3,3,10,10-hexamethyl-9,9-diphenyl-4,8-dioxa-3,9-disilaundecan-5-yl]-3-methyldihydrofuran-2(3H)-one (1015071-58-5)

Guidance literature:

With 1H-imidazole; dmap; In dichloromethane; for 10h; Inert atmosphere; Reflux;

DOI:10.1021/ol8001333

Reference yield:

(3R,S)-1-(tert-Butyldiphenylsilyloxy)pent-4-en-3-ol (147977-33-1) → (3R,5S)-5-[(S)-2,2,3,3,10,10-hexamethyl-9,9-diphenyl-4,8-dioxa-3,9-disilaundecan-5-yl]-3-methyldihydrofuran-2(3H)-one (1015071-58-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 4 h / Reflux

2.1: tert-butyl alcohol; AD-mix-α; methanesulfonamide / water / 24 h / 0 °C

3.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C

3.2: 1 h / -78 °C

With methanesulfonamide; AD-mix-α; lithium hexamethyldisilazane; tert-butyl alcohol; In tetrahydrofuran; water; 1.1: |Julia-Kocienski Olefination;

DOI:10.1055/s-0032-1318141

upstream raw materials:

tert-butyldimethylsilyl chloride

ethyl (E)-7-(tert-butyldiphenylsilyloxy)hept-4-enoate

(3R,S)-1-(tert-Butyldiphenylsilyloxy)pent-4-en-3-ol

(S)-5-[(S)-3-(tert-butyldiphenylsilyloxy)-1-hydroxypropyl]dihydrofuran-2(3H)-one

Downstream raw materials:

(2R,4S,5S)-5-(tert-butyldimethylsilyloxy)-7-(tert-butyldiphenylsilyloxy)-2-methylheptane-1,4-diol

(S)-2,2,3,3,10,10-hexamethyl-9,9-diphenyl-5-[(4S,6R)-2,2,6-trimethyl-1,3-dioxepan-4-yl]-4,8-dioxa-3,9-disilaundecane