2,2-Dimethyl-propionic acid (E)-(2R,6R)-7-(tert-butyl-diphenyl-silanyloxy)-2-[(2S,4R,5R)-5-(2,2-dimethyl-propionyloxymethyl)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-3-hydroxy-4,6-dimethyl-hept-4-enyl ester

Base Information

• Chemical Name: 2,2-Dimethyl-propionic acid (E)-(2R,6R)-7-(tert-butyl-diphenyl-silanyloxy)-2-[(2S,4R,5R)-5-(2,2-dimethyl-propionyloxymethyl)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-3-hydroxy-4,6-dimethyl-hept-4-enyl ester
• CAS No.: 315180-72-4
• Molecular Formula: C₄₇H₆₆O₉Si
• Molecular Weight: 803.121
• Mol file: 315180-72-4.mol

Synonyms:

Chemical Property of 2,2-Dimethyl-propionic acid (E)-(2R,6R)-7-(tert-butyl-diphenyl-silanyloxy)-2-[(2S,4R,5R)-5-(2,2-dimethyl-propionyloxymethyl)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-3-hydroxy-4,6-dimethyl-hept-4-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,2-Dimethyl-propionic acid (E)-(2R,6R)-7-(tert-butyl-diphenyl-silanyloxy)-2-[(2S,4R,5R)-5-(2,2-dimethyl-propionyloxymethyl)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-3-hydroxy-4,6-dimethyl-hept-4-enyl ester

There total 14 articles about 2,2-Dimethyl-propionic acid (E)-(2R,6R)-7-(tert-butyl-diphenyl-silanyloxy)-2-[(2S,4R,5R)-5-(2,2-dimethyl-propionyloxymethyl)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-3-hydroxy-4,6-dimethyl-hept-4-enyl 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:

3-C-(benzyloxymethyl)-3-deoxy-1,2-O-isopropylidene-α-D-allofuranose (85315-68-0) → 2,2-Dimethyl-propionic acid (E)-(2R,6R)-7-(tert-butyl-diphenyl-silanyloxy)-2-[(2S,4R,5R)-5-(2,2-dimethyl-propionyloxymethyl)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-3-hydroxy-4,6-dimethyl-hept-4-enyl ester (315180-72-4)

Guidance literature:

Multi-step reaction with 14 steps

1.1: 86 percent / p-TsOH*H₂O / dimethylformamide / 4 h / 55 °C

2.1: 95 percent / n-Bu₃SnH; MgBr₂ / CH₂Cl₂ / 1 h / 20 °C

3.1: 87 percent / DMSO; (COCl)2; Et₃N / CH₂Cl₂ / 2.5 h / -78 °C

4.1: n-BuLi / hexane; tetrahydrofuran / 0.5 h / 0 °C

4.2: 83 percent / hexane; tetrahydrofuran / 6 h

5.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 24 h / 20 °C

5.2: 66 percent / aq. KOH; H₂O₂ / tetrahydrofuran / 0.5 h

6.1: 99 percent / Et₃N; DMAP / CH₂Cl₂ / 3 h / 20 °C

7.1: 86 percent / 4 N aq. HCl / tetrahydrofuran / 6 h / 55 °C

8.1: Pb(OAc)4 / benzene / 0.17 h / 20 °C

8.2: LiAlH₄ / diethyl ether / 0.33 h / 0 °C

9.1: 84 percent / Et₃N; DMAP / CH₂Cl₂ / 1 h / 20 °C

10.1: 91 percent / H₂ / Raney nickel (W₂) / ethanol / 26 h / 20 °C

11.1: 89 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone; 3 Angstroem molecular sieves / CH₂Cl₂ / 4 h / 20 °C

12.1: Dess-Martin periodinane; pyridine / CH₂Cl₂ / 20 °C

13.1: tert-BuLi / pentane; diethyl ether / 2 h / -78 - 20 °C

13.2: petroleum ether; diethyl ether / 1 h / -78 °C

14.1: Et₃N; DMAP / CH₂Cl₂ / 1 h / 20 °C

With pyridine; lead(IV) acetate; hydrogenchloride; dmap; n-butyllithium; oxalyl dichloride; 3 A molecular sieve; hydrogen; tert.-butyl lithium; tri-n-butyl-tin hydride; Dess-Martin periodane; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; 9-bora-bicyclo[3.3.1]nonane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; magnesium bromide; Raney Nickel (W₂); In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; pentane; benzene; 3.1: Swern oxidation / 4.2: Wittig methylenation;

DOI:10.1248/cpb.48.1761

Reference yield:

3-C-benzyloxymethyl-3,5,6-trideoxy-1,2-O-isopropylidene-5-C-(4-methoxybenzyloxymethyl)-α-D-ribo-hex-5-enofuranose (98039-21-5) → 2,2-Dimethyl-propionic acid (E)-(2R,6R)-7-(tert-butyl-diphenyl-silanyloxy)-2-[(2S,4R,5R)-5-(2,2-dimethyl-propionyloxymethyl)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-3-hydroxy-4,6-dimethyl-hept-4-enyl ester (315180-72-4)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 24 h / 20 °C

1.2: 66 percent / aq. KOH; H₂O₂ / tetrahydrofuran / 0.5 h

2.1: 99 percent / Et₃N; DMAP / CH₂Cl₂ / 3 h / 20 °C

3.1: 86 percent / 4 N aq. HCl / tetrahydrofuran / 6 h / 55 °C

4.1: Pb(OAc)4 / benzene / 0.17 h / 20 °C

4.2: LiAlH₄ / diethyl ether / 0.33 h / 0 °C

5.1: 84 percent / Et₃N; DMAP / CH₂Cl₂ / 1 h / 20 °C

6.1: 91 percent / H₂ / Raney nickel (W₂) / ethanol / 26 h / 20 °C

7.1: 89 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone; 3 Angstroem molecular sieves / CH₂Cl₂ / 4 h / 20 °C

8.1: Dess-Martin periodinane; pyridine / CH₂Cl₂ / 20 °C

9.1: tert-BuLi / pentane; diethyl ether / 2 h / -78 - 20 °C

9.2: petroleum ether; diethyl ether / 1 h / -78 °C

10.1: Et₃N; DMAP / CH₂Cl₂ / 1 h / 20 °C

With pyridine; lead(IV) acetate; hydrogenchloride; dmap; 3 A molecular sieve; hydrogen; tert.-butyl lithium; Dess-Martin periodane; triethylamine; 9-bora-bicyclo[3.3.1]nonane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; Raney Nickel (W₂); In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; pentane; benzene;

DOI:10.1248/cpb.48.1761

Reference yield:

3-C-benzyloxymethyl-3-deoxy-1,2-O-isopropylidene-6-O-(4-methoxybenzyl)-α-D-ribo-hexofuranos-5-ulose (98039-29-3) → 2,2-Dimethyl-propionic acid (E)-(2R,6R)-7-(tert-butyl-diphenyl-silanyloxy)-2-[(2S,4R,5R)-5-(2,2-dimethyl-propionyloxymethyl)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-3-hydroxy-4,6-dimethyl-hept-4-enyl ester (315180-72-4)

Guidance literature:

Multi-step reaction with 11 steps

1.1: n-BuLi / hexane; tetrahydrofuran / 0.5 h / 0 °C

1.2: 83 percent / hexane; tetrahydrofuran / 6 h

2.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 24 h / 20 °C

2.2: 66 percent / aq. KOH; H₂O₂ / tetrahydrofuran / 0.5 h

3.1: 99 percent / Et₃N; DMAP / CH₂Cl₂ / 3 h / 20 °C

4.1: 86 percent / 4 N aq. HCl / tetrahydrofuran / 6 h / 55 °C

5.1: Pb(OAc)4 / benzene / 0.17 h / 20 °C

5.2: LiAlH₄ / diethyl ether / 0.33 h / 0 °C

6.1: 84 percent / Et₃N; DMAP / CH₂Cl₂ / 1 h / 20 °C

7.1: 91 percent / H₂ / Raney nickel (W₂) / ethanol / 26 h / 20 °C

8.1: 89 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone; 3 Angstroem molecular sieves / CH₂Cl₂ / 4 h / 20 °C

9.1: Dess-Martin periodinane; pyridine / CH₂Cl₂ / 20 °C

10.1: tert-BuLi / pentane; diethyl ether / 2 h / -78 - 20 °C

10.2: petroleum ether; diethyl ether / 1 h / -78 °C

11.1: Et₃N; DMAP / CH₂Cl₂ / 1 h / 20 °C

With pyridine; lead(IV) acetate; hydrogenchloride; dmap; n-butyllithium; 3 A molecular sieve; hydrogen; tert.-butyl lithium; Dess-Martin periodane; triethylamine; 9-bora-bicyclo[3.3.1]nonane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; Raney Nickel (W₂); In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; pentane; benzene; 1.2: Wittig methylenation;

DOI:10.1248/cpb.48.1761

upstream raw materials:

pivaloyl chloride

3-C-(benzyloxymethyl)-3-deoxy-1,2-O-isopropylidene-α-D-allofuranose

3-C-benzyloxymethyl-3-deoxy-1,2-O-isopropylidene-6-O-(4-methoxybenzylidene)-α-D-allofuranose

3-C-benzyloxymethyl-3,5,6-trideoxy-1,2-O-isopropylidene-5-C-(4-methoxybenzyloxymethyl)-α-D-ribo-hex-5-enofuranose