(2R,3S,6S,8S,10S)-(+)-10-diphenyl-t-butylsilyloxy-2,3-dimethyl-8-(p-tolylsulphonyloxy)methyl-1,7-dioxaspiro<5.5>undecane

Base Information

• Chemical Name: (2R,3S,6S,8S,10S)-(+)-10-diphenyl-t-butylsilyloxy-2,3-dimethyl-8-(p-tolylsulphonyloxy)methyl-1,7-dioxaspiro<5.5>undecane
• CAS No.: 107865-54-3
• Molecular Formula: C₃₅H₄₆O₆SSi
• Molecular Weight: 622.898
• Mol file: 107865-54-3.mol

Synonyms:(2R,3S,6S,8S,10S)-(+)-10-diphenyl-t-butylsilyloxy-2,3-dimethyl-8-(p-tolylsulphonyloxy)methyl-1,7-dioxaspiro<5.5>undecane

Chemical Property of (2R,3S,6S,8S,10S)-(+)-10-diphenyl-t-butylsilyloxy-2,3-dimethyl-8-(p-tolylsulphonyloxy)methyl-1,7-dioxaspiro<5.5>undecane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,6S,8S,10S)-(+)-10-diphenyl-t-butylsilyloxy-2,3-dimethyl-8-(p-tolylsulphonyloxy)methyl-1,7-dioxaspiro<5.5>undecane

There total 11 articles about (2R,3S,6S,8S,10S)-(+)-10-diphenyl-t-butylsilyloxy-2,3-dimethyl-8-(p-tolylsulphonyloxy)methyl-1,7-dioxaspiro<5.5>undecane 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: 100.0%

(2R,3S,6S,8S,10S)-(+)-2,3-dimethyl-10-hydroxy-8-(p-tolylsulphonyloxy)methyl-1,7-dioxaspiro<5.5>undecane (107692-11-5) + tert-butylchlorodiphenylsilane (58479-61-1) → (2R,3S,6S,8S,10S)-(+)-10-diphenyl-t-butylsilyloxy-2,3-dimethyl-8-(p-tolylsulphonyloxy)methyl-1,7-dioxaspiro<5.5>undecane (107865-54-3)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)84716-4

Reference yield:

(2R,3R)-2-methyl-1-(tetrahydropyran-2-yloxy)butan-2-ol benzyl ether (107692-03-5) → (2R,3S,6S,8S,10S)-(+)-10-diphenyl-t-butylsilyloxy-2,3-dimethyl-8-(p-tolylsulphonyloxy)methyl-1,7-dioxaspiro<5.5>undecane (107865-54-3)

Guidance literature:

Multi-step reaction with 7 steps

1: MeOH / H⁽¹⁺⁾

2: COCl₂, NEt₃ / dimethylsulfoxide

3: tetrahydrofuran / 0 °C

4: n-BuLi / tetrahydrofuran / -80 °C

6: 70 percent / pyridine

7: 100 percent / imidazole / dimethylformamide

With pyridine; 1H-imidazole; methanol; n-butyllithium; triethylamine; hydrogen cation; In tetrahydrofuran; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)84716-4

Reference yield:

(2R,3R)-2-methyl-1-(tetrahydropyran-2-yloxy)butan-2-ol (107692-02-4) → (2R,3S,6S,8S,10S)-(+)-10-diphenyl-t-butylsilyloxy-2,3-dimethyl-8-(p-tolylsulphonyloxy)methyl-1,7-dioxaspiro<5.5>undecane (107865-54-3)

Guidance literature:

Multi-step reaction with 8 steps

1: NaH / tetrahydrofuran

2: MeOH / H⁽¹⁺⁾

3: COCl₂, NEt₃ / dimethylsulfoxide

4: tetrahydrofuran / 0 °C

5: n-BuLi / tetrahydrofuran / -80 °C

7: 70 percent / pyridine

8: 100 percent / imidazole / dimethylformamide

With pyridine; 1H-imidazole; methanol; n-butyllithium; sodium hydride; triethylamine; hydrogen cation; In tetrahydrofuran; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)84716-4

upstream raw materials:

(2R,3S,6S,8S,10S)-(+)-2,3-dimethyl-10-hydroxy-8-(p-tolylsulphonyloxy)methyl-1,7-dioxaspiro<5.5>undecane

tert-butylchlorodiphenylsilane

(2R,3S,6S,8S,10S)-(+)-10-hydroxy-8-hydroxymethyl-2,3-dimethyl-1,7-dioxaspiro<5.5>undecane

(2S,4S,6S,8R,9S)-4-(tert-Butyl-diphenyl-silanyloxy)-8,9-dimethyl-1,7-dioxa-spiro[5.5]undecane-2-carbaldehyde

Downstream raw materials:

(2R,3S,6S,8R,10R)-(+)-10-diphenyl-t-butylsilyloxy-8-cyanomethyl-2,3-dimethyl-1,7-dioxaspiro<5.5>undecane

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

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