2,2-dimethyl-propionic acid 7-[7-(2-benzyloxy-ethyl)-9-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-4,4,8-trimethyl-1,6-dioxa-spiro[4.5]dec-2-yl]-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-7-methoxy-2,4-dimethyl-heptyl ester

Base Information

• Chemical Name: 2,2-dimethyl-propionic acid 7-[7-(2-benzyloxy-ethyl)-9-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-4,4,8-trimethyl-1,6-dioxa-spiro[4.5]dec-2-yl]-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-7-methoxy-2,4-dimethyl-heptyl ester
• CAS No.: 218785-39-8
• Molecular Formula: C₅₃H₁₀₀O₁₀Si₃
• Molecular Weight: 981.627

Synonyms:2,2-dimethyl-propionic acid 7-[7-(2-benzyloxy-ethyl)-9-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-4,4,8-trimethyl-1,6-dioxa-spiro[4.5]dec-2-yl]-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-7-methoxy-2,4-dimethyl-heptyl ester

Chemical Property of 2,2-dimethyl-propionic acid 7-[7-(2-benzyloxy-ethyl)-9-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-4,4,8-trimethyl-1,6-dioxa-spiro[4.5]dec-2-yl]-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-7-methoxy-2,4-dimethyl-heptyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of 2,2-dimethyl-propionic acid 7-[7-(2-benzyloxy-ethyl)-9-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-4,4,8-trimethyl-1,6-dioxa-spiro[4.5]dec-2-yl]-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-7-methoxy-2,4-dimethyl-heptyl ester

There total 32 articles about 2,2-dimethyl-propionic acid 7-[7-(2-benzyloxy-ethyl)-9-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-4,4,8-trimethyl-1,6-dioxa-spiro[4.5]dec-2-yl]-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-7-methoxy-2,4-dimethyl-heptyl ester 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: 92.0%

C61H108O11Si3 (218785-37-6) → 2,2-dimethyl-propionic acid 7-[7-(2-benzyloxy-ethyl)-9-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-4,4,8-trimethyl-1,6-dioxa-spiro[4.5]dec-2-yl]-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-7-methoxy-2,4-dimethyl-heptyl ester (218785-39-8)

Guidance literature:

With water; 2,3-dicyano-5,6-dichloro-p-benzoquinone;

DOI:10.1021/ja992134m

Reference yield:

(3R,4R,5S)-6-(tert-butyldiphenylsiloxy)-4-hydroxy-3,5-dimethylhexan-1-ene (91751-27-8,91797-99-8,91798-00-4,91798-01-5,106357-24-8,106357-26-0,106357-27-1,106357-25-9) → 2,2-dimethyl-propionic acid 7-[7-(2-benzyloxy-ethyl)-9-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-4,4,8-trimethyl-1,6-dioxa-spiro[4.5]dec-2-yl]-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-7-methoxy-2,4-dimethyl-heptyl ester (218785-39-8)

Guidance literature:

Multi-step reaction with 13 steps

1.1: TBAF / tetrahydrofuran

2.1: PPTS

3.1: 86 percent / O₂; aq. Cu(OAc)2; PdCl₂ / N,N-dimethyl-acetamide / 30 h

4.1: 97 percent / KHMDS

5.1: (Bu₃Sn)2; n-BuLi; lithium 2-thienylcyanocuprate

5.2: NBS

6.1: t-BuLi / diethyl ether / 0.5 h / -78 - 0 °C

6.2: lithium 2-thienylcyanocuprate / 0.5 h / -78 - -45 °C

6.3: 83 percent / 48 h / -5 °C

7.1: 96 percent / KHMDS

8.1: OsO₄; NMO

8.2: 87 percent / NaIO₄

9.1: 84 percent / DIBAL

10.1: 51 percent / HO(CH₂)3OH; PPTS / tetrahydrofuran

11.1: pyridine

12.1: 2,6-lutidine

13.1: 92 percent / H₂O; DDQ

With pyridine; 2,6-dimethylpyridine; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; copper diacetate; tetrabutyl ammonium fluoride; water; tert.-butyl lithium; oxygen; bis(tri-n-butyltin); pyridinium p-toluenesulfonate; potassium hexamethylsilazane; diisobutylaluminium hydride; thien-2-yl(cyano)copper lithium; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium dichloride; trimethyleneglycol; In tetrahydrofuran; diethyl ether; N,N-dimethyl acetamide; 1.1: desilylation / 2.1: acetalization / 3.1: Oxidation / 4.1: enol protection / 5.1: Substitution / 5.2: Substitution / 6.1: Metallation / 6.2: Addition / 6.3: coupling / 7.1: Methylation / 8.1: Oxidation / 8.2: cleavage / 9.1: Reduction / 10.1: deprotection / 11.1: Acylation / 12.1: silylation / 13.1: oxidative hydrolysis;

DOI:10.1021/ja992134m

Reference yield:

2-((S)-2,2-Diethyl-[1,3]dioxolan-4-yl)-2-methyl-propan-1-ol (137664-71-2) → 2,2-dimethyl-propionic acid 7-[7-(2-benzyloxy-ethyl)-9-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-4,4,8-trimethyl-1,6-dioxa-spiro[4.5]dec-2-yl]-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-7-methoxy-2,4-dimethyl-heptyl ester (218785-39-8)

Guidance literature:

Multi-step reaction with 20 steps

1.1: DMSO; (COCl)2; Et₃N / CH₂Cl₂ / -78 °C

2.1: BF₃*Et₂O / CH₂Cl₂ / 0 °C

3.1: 85 percent / TsOH / dimethylformamide

4.1: n-BuLi; HMPA / tetrahydrofuran

4.2: 81 percent / DMPU / tetrahydrofuran / -20 °C

5.1: 95 percent / 2,6-lutidine

6.1: 94 percent / DIBAL / CH₂Cl₂ / -78 - 0 °C

7.1: 87 percent / SO₃*pyridine; DMSO; Et₃N / CH₂Cl₂

8.1: tetrahydrofuran / -78 °C

9.1: 95 percent / TBAF / 60 °C

10.1: 76 percent / HgCl₂; CaCO₃ / tetrahydrofuran

11.1: 30 percent aq. H₂O₂; PhCN; KHCO₃ / methanol / 0 °C

12.1: 98 percent / Et₃N

13.1: t-BuLi / diethyl ether / 0.5 h / -78 - 0 °C

13.2: lithium 2-thienylcyanocuprate / 0.5 h / -78 - -45 °C

13.3: 83 percent / 48 h / -5 °C

14.1: 96 percent / KHMDS

15.1: OsO₄; NMO

15.2: 87 percent / NaIO₄

16.1: 84 percent / DIBAL

17.1: 51 percent / HO(CH₂)3OH; PPTS / tetrahydrofuran

18.1: pyridine

19.1: 2,6-lutidine

20.1: 92 percent / H₂O; DDQ

With pyridine; 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; oxalyl dichloride; pyridine-SO₃ complex; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; water; dihydrogen peroxide; tert.-butyl lithium; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; diisobutylaluminium hydride; potassium hydrogencarbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; benzonitrile; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; calcium carbonate; mercury dichloride; trimethyleneglycol; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 1.1: Oxidation / 2.1: thioacetalization; deacetalization / 3.1: acetalization / 4.1: Metallation / 4.2: Addition / 5.1: silylation / 6.1: reductive cleavage / 7.1: Oxidation / 8.1: Grignard reaction / 9.1: desilylation / 10.1: Cyclization / 11.1: Epoxidation / 12.1: silylation / 13.1: Metallation / 13.2: Addition / 13.3: coupling / 14.1: Methylation / 15.1: Oxidation / 15.2: cleavage / 16.1: Reduction / 17.1: deprotection / 18.1: Acylation / 19.1: silylation / 20.1: oxidative hydrolysis;

DOI:10.1021/ja992134m

upstream raw materials:

C₆₁H₁₀₈O₁₁Si₃

t-butyldimethylsiyl triflate

pivaloyl chloride

(3R,4R,5S)-6-(tert-butyldiphenylsiloxy)-4-hydroxy-3,5-dimethylhexan-1-ene

Downstream raw materials:

C₆₃H₁₂₅O₁₃PSi₅

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