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

Base Information

Chemical Name:2,2-Dimethyl-propionic acid (2S,3S,4R,5R,7R)-7-[(2S,3S,5S,7R,8S,9S)-7-(2-benzyloxy-ethyl)-9-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-4,4,8-trimethyl-1,6-dioxa-spiro[4.5]dec-2-yl]-3,5-dihydroxy-7-methoxy-2,4-dimethyl-heptyl ester
CAS No.:254894-52-5
Molecular Formula:C₄₉H₈₀O₁₁Si
Molecular Weight:873.253
Hs Code.:

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

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

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

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

There total 28 articles about 2,2-Dimethyl-propionic acid (2S,3S,4R,5R,7R)-7-[(2S,3S,5S,7R,8S,9S)-7-(2-benzyloxy-ethyl)-9-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-4,4,8-trimethyl-1,6-dioxa-spiro[4.5]dec-2-yl]-3,5-dihydroxy-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:

: 91751-27-8,91797-99-8,91798-00-4,91798-01-5,106357-24-8,106357-26-0,106357-27-1,106357-25-9
(3R,4R,5S)-6-(tert-butyldiphenylsiloxy)-4-hydroxy-3,5-dimethylhexan-1-ene

: 254894-52-5
2,2-Dimethyl-propionic acid (2S,3S,4R,5R,7R)-7-[(2S,3S,5S,7R,8S,9S)-7-(2-benzyloxy-ethyl)-9-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-4,4,8-trimethyl-1,6-dioxa-spiro[4.5]dec-2-yl]-3,5-dihydroxy-7-methoxy-2,4-dimethyl-heptyl ester

Guidance literature:: Multi-step reaction with 11 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

With pyridine; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; copper diacetate; tetrabutyl ammonium fluoride; tert.-butyl lithium; oxygen; bis(tri-n-butyltin); pyridinium p-toluenesulfonate; potassium hexamethylsilazane; diisobutylaluminium hydride; thien-2-yl(cyano)copper lithium; 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;
DOI:10.1021/ja992134m

Reference yield:

: 137664-71-2
2-((S)-2,2-Diethyl-[1,3]dioxolan-4-yl)-2-methyl-propan-1-ol

: 254894-52-5
2,2-Dimethyl-propionic acid (2S,3S,4R,5R,7R)-7-[(2S,3S,5S,7R,8S,9S)-7-(2-benzyloxy-ethyl)-9-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-4,4,8-trimethyl-1,6-dioxa-spiro[4.5]dec-2-yl]-3,5-dihydroxy-7-methoxy-2,4-dimethyl-heptyl ester

Guidance literature:: Multi-step reaction with 18 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

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; dihydrogen peroxide; tert.-butyl lithium; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; diisobutylaluminium hydride; potassium hydrogencarbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; benzonitrile; triethylamine; 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;
DOI:10.1021/ja992134m

Reference yield:

: 137664-76-7
(S)-3-[1,3]Dithian-2-yl-3-methyl-butane-1,2-diol

: 254894-52-5
2,2-Dimethyl-propionic acid (2S,3S,4R,5R,7R)-7-[(2S,3S,5S,7R,8S,9S)-7-(2-benzyloxy-ethyl)-9-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-4,4,8-trimethyl-1,6-dioxa-spiro[4.5]dec-2-yl]-3,5-dihydroxy-7-methoxy-2,4-dimethyl-heptyl ester

Guidance literature:: Multi-step reaction with 16 steps

1.1: 85 percent / TsOH / dimethylformamide

2.1: n-BuLi; HMPA / tetrahydrofuran

2.2: 81 percent / DMPU / tetrahydrofuran / -20 °C

3.1: 95 percent / 2,6-lutidine

4.1: 94 percent / DIBAL / CH₂Cl₂ / -78 - 0 °C

5.1: 87 percent / SO₃*pyridine; DMSO; Et₃N / CH₂Cl₂

6.1: tetrahydrofuran / -78 °C

7.1: 95 percent / TBAF / 60 °C

8.1: 76 percent / HgCl₂; CaCO₃ / tetrahydrofuran

9.1: 30 percent aq. H₂O₂; PhCN; KHCO₃ / methanol / 0 °C

10.1: 98 percent / Et₃N

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

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

11.3: 83 percent / 48 h / -5 °C

12.1: 96 percent / KHMDS

13.1: OsO₄; NMO

13.2: 87 percent / NaIO₄

14.1: 84 percent / DIBAL

15.1: 51 percent / HO(CH₂)3OH; PPTS / tetrahydrofuran

16.1: pyridine

With pyridine; 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; pyridine-SO₃ complex; tetrabutyl ammonium fluoride; dihydrogen peroxide; tert.-butyl lithium; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; diisobutylaluminium hydride; potassium hydrogencarbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; benzonitrile; triethylamine; calcium carbonate; mercury dichloride; trimethyleneglycol; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 1.1: acetalization / 2.1: Metallation / 2.2: Addition / 3.1: silylation / 4.1: reductive cleavage / 5.1: Oxidation / 6.1: Grignard reaction / 7.1: desilylation / 8.1: Cyclization / 9.1: Epoxidation / 10.1: silylation / 11.1: Metallation / 11.2: Addition / 11.3: coupling / 12.1: Methylation / 13.1: Oxidation / 13.2: cleavage / 14.1: Reduction / 15.1: deprotection / 16.1: Acylation;
DOI:10.1021/ja992134m