(2R,6R,8S)-8-(2-Benzyloxy-ethyl)-10-(tert-butyl-dimethyl-silanyloxy)-2-vinyl-1,7-dioxa-spiro[5.5]undecan-4-one

Base Information

• Chemical Name: (2R,6R,8S)-8-(2-Benzyloxy-ethyl)-10-(tert-butyl-dimethyl-silanyloxy)-2-vinyl-1,7-dioxa-spiro[5.5]undecan-4-one
• CAS No.: 215160-84-2
• Molecular Formula: C₂₆H₄₀O₅Si
• Molecular Weight: 460.686
• Mol file: 215160-84-2.mol

Synonyms:(2R,6R,8S)-8-(2-Benzyloxy-ethyl)-10-(tert-butyl-dimethyl-silanyloxy)-2-vinyl-1,7-dioxa-spiro[5.5]undecan-4-one

Chemical Property of (2R,6R,8S)-8-(2-Benzyloxy-ethyl)-10-(tert-butyl-dimethyl-silanyloxy)-2-vinyl-1,7-dioxa-spiro[5.5]undecan-4-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,6R,8S)-8-(2-Benzyloxy-ethyl)-10-(tert-butyl-dimethyl-silanyloxy)-2-vinyl-1,7-dioxa-spiro[5.5]undecan-4-one

There total 12 articles about (2R,6R,8S)-8-(2-Benzyloxy-ethyl)-10-(tert-butyl-dimethyl-silanyloxy)-2-vinyl-1,7-dioxa-spiro[5.5]undecan-4-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: 73.0%

vinyl magnesium bromide (1826-67-1) + (6R,8S)-8-(2-Benzyloxy-ethyl)-10-(tert-butyl-dimethyl-silanyloxy)-1,7-dioxa-spiro[5.5]undec-2-en-4-one (215160-83-1) → (2R,6R,8S)-8-(2-Benzyloxy-ethyl)-10-(tert-butyl-dimethyl-silanyloxy)-2-vinyl-1,7-dioxa-spiro[5.5]undecan-4-one (215160-84-2)

Guidance literature:

With 4; In tetrahydrofuran;

DOI:10.1016/S0040-4039(98)01629-3

Reference yield:

2-methyl-4H-pyran-4-one (5848-33-9) → (2R,6R,8S)-8-(2-Benzyloxy-ethyl)-10-(tert-butyl-dimethyl-silanyloxy)-2-vinyl-1,7-dioxa-spiro[5.5]undecan-4-one (215160-84-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 78 percent / LiHMDS / tetrahydrofuran / -78 °C

2: lutidine / CH₂Cl₂

3: DDQ / CH₂Cl₂

4: 93 percent / CF₃COOH / benzene / 96 h

5: 73 percent / 3PCuI>4 / tetrahydrofuran

With 4; lutidine; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; benzene;

DOI:10.1016/S0040-4039(98)01629-3

Reference yield:

3-benzyloxypropan-1-ol (4799-68-2) → (2R,6R,8S)-8-(2-Benzyloxy-ethyl)-10-(tert-butyl-dimethyl-silanyloxy)-2-vinyl-1,7-dioxa-spiro[5.5]undecan-4-one (215160-84-2)

Guidance literature:

Multi-step reaction with 9 steps

1: DMSO, (COCl)2, Et₃N

2: 87 percent / tetrahydrofuran; diethyl ether

3: 85 percent / NaH / dimethylformamide

4: 93 percent / OsO₄, NaIO₄

5: 78 percent / LiHMDS / tetrahydrofuran / -78 °C

6: lutidine / CH₂Cl₂

7: DDQ / CH₂Cl₂

8: 93 percent / CF₃COOH / benzene / 96 h

9: 73 percent / 3PCuI>4 / tetrahydrofuran

With sodium periodate; osmium(VIII) oxide; oxalyl dichloride; 4; lutidine; sodium hydride; dimethyl sulfoxide; triethylamine; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; benzene;

DOI:10.1016/S0040-4039(98)01629-3

upstream raw materials:

vinyl magnesium bromide

(6R,8S)-8-(2-Benzyloxy-ethyl)-10-(tert-butyl-dimethyl-silanyloxy)-1,7-dioxa-spiro[5.5]undec-2-en-4-one

2-methyl-4H-pyran-4-one

3-benzyloxypropan-1-ol

Downstream raw materials:

(2R,4S,6R,8S)-8-(2-Benzyloxy-ethyl)-10-(tert-butyl-dimethyl-silanyloxy)-4-methyl-2-vinyl-1,7-dioxa-spiro[5.5]undecan-4-ol

(2S,6S,8R,10S)-2-(2-Benzyloxy-ethyl)-10-hydroxy-10-methyl-8-vinyl-1,7-dioxa-spiro[5.5]undecan-4-one

(2R,4S,6R,8S,10S)-8-(2-Benzyloxy-ethyl)-4-methyl-2-vinyl-1,7-dioxa-spiro[5.5]undecane-4,10-diol