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

Base Information

• Chemical Name: (2R,3S,6S,8R,10R)-(+)-10-diphenyl-t-butylsilyloxy-8-cyanomethyl-2,3-dimethyl-1,7-dioxaspiro<5.5>undecane
• CAS No.: 107692-12-6
• Molecular Formula: C₂₉H₃₉NO₃Si
• Molecular Weight: 477.719
• Mol file: 107692-12-6.mol

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

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

There total 12 articles about (2R,3S,6S,8R,10R)-(+)-10-diphenyl-t-butylsilyloxy-8-cyanomethyl-2,3-dimethyl-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: 80.0%

sodium cyanide (143-33-9,25596-52-5) + (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) → (2R,3S,6S,8R,10R)-(+)-10-diphenyl-t-butylsilyloxy-8-cyanomethyl-2,3-dimethyl-1,7-dioxaspiro<5.5>undecane (107692-12-6)

Guidance literature:

In dimethyl sulfoxide; at 80 ℃;

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,8R,10R)-(+)-10-diphenyl-t-butylsilyloxy-8-cyanomethyl-2,3-dimethyl-1,7-dioxaspiro<5.5>undecane (107692-12-6)

Guidance literature:

Multi-step reaction with 8 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

8: 80 percent / dimethylsulfoxide / 80 °C

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,8R,10R)-(+)-10-diphenyl-t-butylsilyloxy-8-cyanomethyl-2,3-dimethyl-1,7-dioxaspiro<5.5>undecane (107692-12-6)

Guidance literature:

Multi-step reaction with 9 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

9: 80 percent / dimethylsulfoxide / 80 °C

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:

sodium cyanide

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

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

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

Downstream raw materials:

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

(2R,2'R,3'S,6'S,8'R,10'R)-2,4-dimethyl-(10'-diphenyl-t-butylsiloxy-2',3'-dimethyl-1',7'-dioxaspiro<5.5>undecan-8-yl)-hex-4-enoyl 4S-(propan-2-yl)oxazolidin-2-one