1,3,7-Octanetriol,5-methylene-8-[(2S,4R,6R)-tetrahydro-6-[2-[[(4-methoxyphenyl)methoxy]methyl]-4-oxazolyl]-4-[[tris(1-methylethyl)silyl]oxy]-2H-pyran-2-yl]-,7-methanesulfonate, (3R)-

Base Information

• Chemical Name: 1,3,7-Octanetriol,5-methylene-8-[(2S,4R,6R)-tetrahydro-6-[2-[[(4-methoxyphenyl)methoxy]methyl]-4-oxazolyl]-4-[[tris(1-methylethyl)silyl]oxy]-2H-pyran-2-yl]-,7-methanesulfonate, (3R)-
• CAS No.: 265666-25-9
• Molecular Formula: C36H59NO10SSi
• Molecular Weight: 726.017
• Mol file: 265666-25-9.mol

Synonyms:

Chemical Property of 1,3,7-Octanetriol,5-methylene-8-[(2S,4R,6R)-tetrahydro-6-[2-[[(4-methoxyphenyl)methoxy]methyl]-4-oxazolyl]-4-[[tris(1-methylethyl)silyl]oxy]-2H-pyran-2-yl]-,7-methanesulfonate, (3R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,3,7-Octanetriol,5-methylene-8-[(2S,4R,6R)-tetrahydro-6-[2-[[(4-methoxyphenyl)methoxy]methyl]-4-oxazolyl]-4-[[tris(1-methylethyl)silyl]oxy]-2H-pyran-2-yl]-,7-methanesulfonate, (3R)-

There total 28 articles about 1,3,7-Octanetriol,5-methylene-8-[(2S,4R,6R)-tetrahydro-6-[2-[[(4-methoxyphenyl)methoxy]methyl]-4-oxazolyl]-4-[[tris(1-methylethyl)silyl]oxy]-2H-pyran-2-yl]-,7-methanesulfonate, (3R)- 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:

Methanesulfonic acid 3-((R)-2,2-dimethyl-[1,3]dioxan-4-ylmethyl)-1-{(2S,4R,6R)-6-[2-(4-methoxy-benzyloxymethyl)-oxazol-4-yl]-4-triisopropylsilanyloxy-tetrahydro-pyran-2-ylmethyl}-but-3-enyl ester (657389-92-9) → (2'S,4'R,6'R,5R)-methanesulfonic acid 5,7-dihydroxy-1-{6'-[2-(4-methoxybenzyloxymethyl)-oxazol-4-yl]-4'-(triisopropylsilanyloxy)-tetrahydropyran-2'-yl-methyl}-3-methyleneheptyl ester (265666-25-9)

Guidance literature:

With camphor-10-sulfonic acid; In methanol;

DOI:10.1016/S0040-4039(99)02187-5

Reference yield:

(4S,1'R)-4-(1'-hydroxybut-3'-enyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester (132328-52-0) → (2'S,4'R,6'R,5R)-methanesulfonic acid 5,7-dihydroxy-1-{6'-[2-(4-methoxybenzyloxymethyl)-oxazol-4-yl]-4'-(triisopropylsilanyloxy)-tetrahydropyran-2'-yl-methyl}-3-methyleneheptyl ester (265666-25-9)

Guidance literature:

Multi-step reaction with 19 steps

1.1: 90 percent / DMAP; Et₃N / CH₂Cl₂ / 12 h / 20 °C

2.1: O₃; NaHCO₃ / CH₂Cl₂ / 1 h / -78 °C

2.2: 92 percent / PPh₃ / CH₂Cl₂ / 14 h / -78 - 20 °C

3.1: diethyl ether / 2.25 h / -78 °C

3.2: 76 percent / Et₃N; aq. H₂O₂ / diethyl ether / 12 h / 20 °C

4.1: 92 percent / 2,6-lutidine / CH₂Cl₂ / 1.25 h / -78 °C

5.1: ozone; NaHCO₃ / CH₂Cl₂ / 0.5 h / -78 °C

5.2: 95 percent / PPh₃ / CH₂Cl₂ / 14 h / 20 °C

6.1: 87 percent / CH₂Cl₂ / 14 h / 20 °C

7.1: 84 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 4 h / 20 °C

8.1: 87 percent / NaHMDS / tetrahydrofuran / 1 h / -78 °C

9.1: aq. HCl / dioxane / 1.33 h / 20 °C

10.1: 1.34 g / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; 1-hydroxybenzotriazole; Et₃N / tetrahydrofuran / 20 h / 20 °C

11.1: Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

12.1: PPh₃; 2,6-di-tert-butylpyridine; dibromotetrachloroethane / CH₂Cl₂ / 3 h / 20 °C

12.2: 0.65 g / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂; acetonitrile / 1 h / 20 °C

13.1: 87 percent / DIBALH / toluene / 2.5 h / -78 °C

14.1: n-BuLi / hexane; tetrahydrofuran / 1 h / 0 °C

14.2: 59 percent / hexane; tetrahydrofuran / 16 h / -78 - 20 °C

15.1: 50 percent / (DHQD)2PYR; K₂OsO₂(OH)4; K₃Fe(CN)6 / aq. K₂CO₃ / 2-methyl-propan-2-ol

16.1: NaH / tetrahydrofuran / 1 h / 20 °C

16.2: 76 percent / N-tosylimidazole / tetrahydrofuran / 3 h / 0 - 20 °C

17.1: t-BuLi / pentane; tetrahydrofuran / 0.5 h / -78 °C

17.2: lithium 2-thienylcyanocuprate / pentane; tetrahydrofuran / 1 h / -40 °C

17.3: 20 percent / pentane; tetrahydrofuran / 24 h / -78 - 0 °C

18.1: Et₃N / CH₂Cl₂ / 0.75 h / 0 °C

19.1: 25 mg / 10-camphorsulfonic acid / methanol / 1.5 h / 20 °C

With 2,6-dimethylpyridine; hydrogenchloride; dmap; n-butyllithium; 2,6-di-tert-butyl-pyridine; hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether; potassium dioxotetrahydroxoosmate(VI); dibromotetrachloroethane; (1S)-10-camphorsulfonic acid; tert.-butyl lithium; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; benzotriazol-1-ol; Dess-Martin periodane; ozone; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; triphenylphosphine; potassium hexacyanoferrate(III); potassium carbonate; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; hexane; dichloromethane; toluene; tert-butyl alcohol; pentane; 6.1: Wittig reaction / 8.1: oxy-anion intramolecular Michael reaction;

DOI:10.1039/b308305e

Reference yield:

(4S,1'R)-2,2-dimethyl-4-[1'-(triethylsilanyloxy)-but-3'-enyl]-oxazolidine-3-carboxylic acid tert-butyl ester (265666-28-2) → (2'S,4'R,6'R,5R)-methanesulfonic acid 5,7-dihydroxy-1-{6'-[2-(4-methoxybenzyloxymethyl)-oxazol-4-yl]-4'-(triisopropylsilanyloxy)-tetrahydropyran-2'-yl-methyl}-3-methyleneheptyl ester (265666-25-9)

Guidance literature:

Multi-step reaction with 18 steps

1.1: O₃; NaHCO₃ / CH₂Cl₂ / 1 h / -78 °C

1.2: 92 percent / PPh₃ / CH₂Cl₂ / 14 h / -78 - 20 °C

2.1: diethyl ether / 2.25 h / -78 °C

2.2: 76 percent / Et₃N; aq. H₂O₂ / diethyl ether / 12 h / 20 °C

3.1: 92 percent / 2,6-lutidine / CH₂Cl₂ / 1.25 h / -78 °C

4.1: ozone; NaHCO₃ / CH₂Cl₂ / 0.5 h / -78 °C

4.2: 95 percent / PPh₃ / CH₂Cl₂ / 14 h / 20 °C

5.1: 87 percent / CH₂Cl₂ / 14 h / 20 °C

6.1: 84 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 4 h / 20 °C

7.1: 87 percent / NaHMDS / tetrahydrofuran / 1 h / -78 °C

8.1: aq. HCl / dioxane / 1.33 h / 20 °C

9.1: 1.34 g / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; 1-hydroxybenzotriazole; Et₃N / tetrahydrofuran / 20 h / 20 °C

10.1: Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

11.1: PPh₃; 2,6-di-tert-butylpyridine; dibromotetrachloroethane / CH₂Cl₂ / 3 h / 20 °C

11.2: 0.65 g / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂; acetonitrile / 1 h / 20 °C

12.1: 87 percent / DIBALH / toluene / 2.5 h / -78 °C

13.1: n-BuLi / hexane; tetrahydrofuran / 1 h / 0 °C

13.2: 59 percent / hexane; tetrahydrofuran / 16 h / -78 - 20 °C

14.1: 50 percent / (DHQD)2PYR; K₂OsO₂(OH)4; K₃Fe(CN)6 / aq. K₂CO₃ / 2-methyl-propan-2-ol

15.1: NaH / tetrahydrofuran / 1 h / 20 °C

15.2: 76 percent / N-tosylimidazole / tetrahydrofuran / 3 h / 0 - 20 °C

16.1: t-BuLi / pentane; tetrahydrofuran / 0.5 h / -78 °C

16.2: lithium 2-thienylcyanocuprate / pentane; tetrahydrofuran / 1 h / -40 °C

16.3: 20 percent / pentane; tetrahydrofuran / 24 h / -78 - 0 °C

17.1: Et₃N / CH₂Cl₂ / 0.75 h / 0 °C

18.1: 25 mg / 10-camphorsulfonic acid / methanol / 1.5 h / 20 °C

With 2,6-dimethylpyridine; hydrogenchloride; n-butyllithium; 2,6-di-tert-butyl-pyridine; hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether; potassium dioxotetrahydroxoosmate(VI); dibromotetrachloroethane; (1S)-10-camphorsulfonic acid; tert.-butyl lithium; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; benzotriazol-1-ol; Dess-Martin periodane; ozone; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; triphenylphosphine; potassium hexacyanoferrate(III); potassium carbonate; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; hexane; dichloromethane; toluene; tert-butyl alcohol; pentane; 5.1: Wittig reaction / 7.1: oxy-anion intramolecular Michael reaction;

DOI:10.1039/b308305e

upstream raw materials:

Methanesulfonic acid 3-((R)-2,2-dimethyl-[1,3]dioxan-4-ylmethyl)-1-{(2S,4R,6R)-6-[2-(4-methoxy-benzyloxymethyl)-oxazol-4-yl]-4-triisopropylsilanyloxy-tetrahydro-pyran-2-ylmethyl}-but-3-enyl ester

p-methoxybenzyloxy acetic acid

(4S,1'R)-4-(1'-hydroxybut-3'-enyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

(4S)-4-(2'-iodo-allyl)-2,2-dimethyl-[1,3]-dioxane

Downstream raw materials:

(2'R,4'R,6'R,2R,6R)-2''-({6'-[2-(4-methoxybenzyloxymethyl)-oxazol-4-yl]-4'-(triisopropylsilanyloxy)-tetrahydropyran-2'-yl-methyl}-4-methylene-tetrahydropyran-2-yl)-ethanol

4-((2R,4R,6R)-6-{(2R,6R)-6-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-methylene-tetrahydro-pyran-2-ylmethyl}-4-triisopropylsilanyloxy-tetrahydro-pyran-2-yl)-2-(4-methoxy-benzyloxymethyl)-oxazole