(2R,3S,6S,10R)-(E)-(+)-10-diphenyl-t-butylsiloxy-8<(5'R)-3',5'-dimethyl-6'thiophenylhex-2'-enyl>-2,3-dimethyl-1,7-dioxaspiro<5.5>undecan

Base Information

• Chemical Name: (2R,3S,6S,10R)-(E)-(+)-10-diphenyl-t-butylsiloxy-8<(5'R)-3',5'-dimethyl-6'thiophenylhex-2'-enyl>-2,3-dimethyl-1,7-dioxaspiro<5.5>undecan
• CAS No.: 101212-44-6
• Molecular Formula: C₄₁H₅₆O₃SSi
• Molecular Weight: 657.045
• Mol file: 101212-44-6.mol

Synonyms:(2R,3S,6S,10R)-(E)-(+)-10-diphenyl-t-butylsiloxy-8<(5'R)-3',5'-dimethyl-6'thiophenylhex-2'-enyl>-2,3-dimethyl-1,7-dioxaspiro<5.5>undecan

Chemical Property of (2R,3S,6S,10R)-(E)-(+)-10-diphenyl-t-butylsiloxy-8<(5'R)-3',5'-dimethyl-6'thiophenylhex-2'-enyl>-2,3-dimethyl-1,7-dioxaspiro<5.5>undecan

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,6S,10R)-(E)-(+)-10-diphenyl-t-butylsiloxy-8<(5'R)-3',5'-dimethyl-6'thiophenylhex-2'-enyl>-2,3-dimethyl-1,7-dioxaspiro<5.5>undecan

There total 32 articles about (2R,3S,6S,10R)-(E)-(+)-10-diphenyl-t-butylsiloxy-8<(5'R)-3',5'-dimethyl-6'thiophenylhex-2'-enyl>-2,3-dimethyl-1,7-dioxaspiro<5.5>undecan 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: 90.0%

(2R,2'R,3'S,6'S,8'R,10'R)-(+)-6-(10'-diphenyl-t-butylsiloxy-2',3'-dimethyl-1',7'-dioxaspiro<5.5>undecan-8'-yl)-2,4-dimethylhex-4-enyl toluene-p-sulphonate (113016-73-2) + thiophenol (108-98-5) → (2R,3S,6S,10R)-(E)-(+)-10-diphenyl-t-butylsiloxy-8<(5'R)-3',5'-dimethyl-6'thiophenylhex-2'-enyl>-2,3-dimethyl-1,7-dioxaspiro<5.5>undecan (101212-44-6)

Guidance literature:

With sodium; In methanol; Ambient temperature;

Reference yield: 55.0%

(3RS,5R,2'R,3'S,6'S,8'S,10'R)-O-3-(10'-diphenyl-t-butylsiloxy-2',3'-dimethyl-1'7'-dioxaspiro<5.5>undecan-8'-yl)-3,5-dimethyl-6-thiophenylhex-1-enyl S-methyl thiocarbonate (112995-98-9,113083-42-4) → (2R,3S,6S,10R)-(E)-(+)-10-diphenyl-t-butylsiloxy-8<(5'R)-3',5'-dimethyl-6'thiophenylhex-2'-enyl>-2,3-dimethyl-1,7-dioxaspiro<5.5>undecan (101212-44-6)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; for 2h; Heating;

Reference yield:

(2R,3S,6S,8S,10S)-(+)-2,3-dimethyl-10-hydroxy-8-(p-tolylsulphonyloxy)methyl-1,7-dioxaspiro<5.5>undecane (107692-11-5) → (2R,3S,6S,10R)-(E)-(+)-10-diphenyl-t-butylsiloxy-8<(5'R)-3',5'-dimethyl-6'thiophenylhex-2'-enyl>-2,3-dimethyl-1,7-dioxaspiro<5.5>undecan (101212-44-6)

Guidance literature:

Multi-step reaction with 11 steps

1: 88 percent / imidazole / dimethylformamide / Ambient temperature

2: 80 percent / dimethylformamide / 12 h / 70 °C

3: di-isobutylaluminium hydride / CH₂Cl₂ / 5 h / Ambient temperature; 1.) -78 deg C --> room temp., 1 h

4: CH₂Cl₂ / 0 deg C, then room temp. overnight

5: 60 percent / di-isobutylaluminium hydride / tetrahydrofuran; diethyl ether / 1 h / -78 °C / -78 deg C --> room temp., overnight

6: triethylamine, dimethylaminopyridine / CH₂Cl₂ / 0 °C

7: sodium iodide / tetrahydrofuran / 12 h

8: 80 percent / tetrahydrofuran / -20 °C

9: lithium aluminium hydride / diethyl ether / 1 h / 0 °C

10: pyridine / 0 °C

11: 90 percent / sodium / methanol / Ambient temperature

With 1H-imidazole; dmap; lithium aluminium tetrahydride; diisobutylaluminum hydride; sodium; triethylamine; sodium iodide; In tetrahydrofuran; pyridine; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

upstream raw materials:

(2R,2'R,3'S,6'S,8'R,10'R)-(+)-6-(10'-diphenyl-t-butylsiloxy-2',3'-dimethyl-1',7'-dioxaspiro<5.5>undecan-8'-yl)-2,4-dimethylhex-4-enyl toluene-p-sulphonate

thiophenol

(3RS,5R,2'R,3'S,6'S,8'S,10'R)-O-3-(10'-diphenyl-t-butylsiloxy-2',3'-dimethyl-1'7'-dioxaspiro<5.5>undecan-8'-yl)-3,5-dimethyl-6-thiophenylhex-1-enyl S-methyl thiocarbonate

iodomethyl phenyl sulfide

Downstream raw materials:

methyl 2-<(6'R)-(10-diphenyl-t-butylsiloxy-2,3-dimethyl-1,7-dioxaspiro<5.5>undecan-8-yl)-6',8'-dimethyldecan-2',4',8'-trien-2'-yl>-4-methoxy-5-methylbenzoate

methyl 2-<(6R)-10-(10-hydroxy-2,3-dimethyl-1,7-dioxaspiro<5.5>undecan-8-yl)-6,8-dimethyldecan-2,4,8-trien-2-yl>-4-methoxy-5-methylbenzoate

2-{(1E,7E)-(R)-4-Benzenesulfonyl-3-benzoyloxy-9-[(2R,4S,6R,8R,9S)-4-(tert-butyl-diphenyl-silanyloxy)-8,9-dimethyl-1,7-dioxa-spiro[5.5]undec-2-yl]-1,5,7-trimethyl-nona-1,7-dienyl}-4-methoxy-5-methyl-benzoic acid methyl ester

(2R,3S,6S,10R)-(E)-(+)-10-diphenyl-t-butylsiloxy-8<(5'R)-3',5'-dimethyl-6'-phenylsulphonylhex-2'-enyl>-2,3-dimethyl-1,7-dioxaspiro<5.5>undecan