(2S,3S,4R,5R,6S,7R)-5-(4-methoxy-benzyloxy)-4,6-dimethyl-2,3-epoxy-9-decene-1,7-diol

Base Information

• Chemical Name: (2S,3S,4R,5R,6S,7R)-5-(4-methoxy-benzyloxy)-4,6-dimethyl-2,3-epoxy-9-decene-1,7-diol
• CAS No.: 201854-69-5
• Molecular Formula: C₂₀H₃₀O₅
• Molecular Weight: 350.455
• Mol file: 201854-69-5.mol

Synonyms:(2S,3S,4R,5R,6S,7R)-5-(4-methoxy-benzyloxy)-4,6-dimethyl-2,3-epoxy-9-decene-1,7-diol

Chemical Property of (2S,3S,4R,5R,6S,7R)-5-(4-methoxy-benzyloxy)-4,6-dimethyl-2,3-epoxy-9-decene-1,7-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4R,5R,6S,7R)-5-(4-methoxy-benzyloxy)-4,6-dimethyl-2,3-epoxy-9-decene-1,7-diol

There total 9 articles about (2S,3S,4R,5R,6S,7R)-5-(4-methoxy-benzyloxy)-4,6-dimethyl-2,3-epoxy-9-decene-1,7-diol 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: 86.0%

(2S,3S,4R,5R,6S,7R)-5-(4-methoxy-benzyloxy)-4,6-dimethyl-2,3-epoxy-7-triethyl-silanyloxy-9-decene-1-ol (201854-76-4) → (2S,3S,4R,5R,6S,7R)-5-(4-methoxy-benzyloxy)-4,6-dimethyl-2,3-epoxy-9-decene-1,7-diol (201854-69-5)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 1.5h;

DOI:10.1039/b308305e

Reference yield:

1-(tert-butyl-diphenyl-silanyloxy)-2,4-dimethyl-hex-5-en-3-ol → (2S,3S,4R,5R,6S,7R)-5-(4-methoxy-benzyloxy)-4,6-dimethyl-2,3-epoxy-9-decene-1,7-diol (201854-69-5)

Guidance literature:

Multi-step reaction with 13 steps

1.1: CF₃SO₃H / diethyl ether / 0.17 h / 0 °C

2.1: 371 mg / TBAF / tetrahydrofuran / 1 h / 20 °C

3.1: 91 percent / pyridine; DMAP / 3 h / 25 °C

4.1: OsO₄; aq. NMO / acetone / 12 h / 20 °C

5.1: 3.2 g / aq. NaIO₄ / tetrahydrofuran / 0 °C / pH 7

6.1: 94 percent / BF₃*Et₂O / CH₂Cl₂ / 2 h / -78 °C

7.1: 2,6-lutidine / CH₂Cl₂ / -50 °C

8.1: 347 mg / DIBALH / toluene; hexane / 2 h / -78 °C

9.1: DMSO; (COCl)2; Et₃N / CH₂Cl₂ / 1.5 h / -70 - -30 °C

10.1: NaHMDS / tetrahydrofuran / 0.17 h / 0 °C

10.2: 309 mg / tetrahydrofuran / 1 h / -78 °C

11.1: 89 percent / DIBAL-H / toluene; hexane / 2 h / -78 °C

12.1: 98 percent / L-(+)-diethyl tartrate; Ti(i-OPr)4; t-BuOOH / 4 Angstroem molecular sieves / CH₂Cl₂; decane / 14.5 h / -25 - -20 °C

13.1: 86 percent / TBAF / tetrahydrofuran / 1.5 h / 0 °C

With pyridine; 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; oxalyl dichloride; diethyl (2R,3R)-tartrate; trifluorormethanesulfonic acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; 4 A molecular sieve; In tetrahydrofuran; diethyl ether; decane; hexane; dichloromethane; acetone; toluene; 10.2: Wadsworth-Emmons olefination / 12.1: Sharpless reaction;

DOI:10.1039/b308305e

Reference yield:

Benzoic acid (S)-3-(4-methoxy-benzyloxy)-2,4-dimethyl-5-triethylsilanyloxy-oct-7-enyl ester → (2S,3S,4R,5R,6S,7R)-5-(4-methoxy-benzyloxy)-4,6-dimethyl-2,3-epoxy-9-decene-1,7-diol (201854-69-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 347 mg / DIBALH / toluene; hexane / 2 h / -78 °C

2.1: DMSO; (COCl)2; Et₃N / CH₂Cl₂ / 1.5 h / -70 - -30 °C

3.1: NaHMDS / tetrahydrofuran / 0.17 h / 0 °C

3.2: 309 mg / tetrahydrofuran / 1 h / -78 °C

4.1: 89 percent / DIBAL-H / toluene; hexane / 2 h / -78 °C

5.1: 98 percent / L-(+)-diethyl tartrate; Ti(i-OPr)4; t-BuOOH / 4 Angstroem molecular sieves / CH₂Cl₂; decane / 14.5 h / -25 - -20 °C

6.1: 86 percent / TBAF / tetrahydrofuran / 1.5 h / 0 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; oxalyl dichloride; diethyl (2R,3R)-tartrate; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; 4 A molecular sieve; In tetrahydrofuran; decane; hexane; dichloromethane; toluene; 3.2: Wadsworth-Emmons olefination / 5.1: Sharpless reaction;

DOI:10.1039/b308305e

upstream raw materials:

(2S,3S,4R,5R,6S,7R)-5-(4-methoxy-benzyloxy)-4,6-dimethyl-2,3-epoxy-7-triethyl-silanyloxy-9-decene-1-ol

Downstream raw materials:

1-[6-allyl-4-(4-methoxy-benzyloxy)-3,5-dimethyl-tetrahydropyran-2-yl]-ethane-1,2-diol