(2R,3R)-2-[(1S,2R,5S,6S,7R,8S)-10-Benzenesulfonyl-2-(3,4-dimethoxy-benzyloxymethoxy)-1,5,7-trimethyl-6,8-bis-triethylsilanyloxy-decyl]-5-methoxy-3-methyl-tetrahydro-furan

Base Information

• Chemical Name: (2R,3R)-2-[(1S,2R,5S,6S,7R,8S)-10-Benzenesulfonyl-2-(3,4-dimethoxy-benzyloxymethoxy)-1,5,7-trimethyl-6,8-bis-triethylsilanyloxy-decyl]-5-methoxy-3-methyl-tetrahydro-furan
• CAS No.: 188359-30-0
• Molecular Formula: C₄₇H₈₂O₁₀SSi₂
• Molecular Weight: 895.399
• Mol file: 188359-30-0.mol

Synonyms:(2R,3R)-2-[(1S,2R,5S,6S,7R,8S)-10-Benzenesulfonyl-2-(3,4-dimethoxy-benzyloxymethoxy)-1,5,7-trimethyl-6,8-bis-triethylsilanyloxy-decyl]-5-methoxy-3-methyl-tetrahydro-furan

Chemical Property of (2R,3R)-2-[(1S,2R,5S,6S,7R,8S)-10-Benzenesulfonyl-2-(3,4-dimethoxy-benzyloxymethoxy)-1,5,7-trimethyl-6,8-bis-triethylsilanyloxy-decyl]-5-methoxy-3-methyl-tetrahydro-furan

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R)-2-[(1S,2R,5S,6S,7R,8S)-10-Benzenesulfonyl-2-(3,4-dimethoxy-benzyloxymethoxy)-1,5,7-trimethyl-6,8-bis-triethylsilanyloxy-decyl]-5-methoxy-3-methyl-tetrahydro-furan

There total 33 articles about (2R,3R)-2-[(1S,2R,5S,6S,7R,8S)-10-Benzenesulfonyl-2-(3,4-dimethoxy-benzyloxymethoxy)-1,5,7-trimethyl-6,8-bis-triethylsilanyloxy-decyl]-5-methoxy-3-methyl-tetrahydro-furan 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: 98.0%

<(3,4-dimethoxybenzyl)oxy>methyl chloride (67680-46-0) + (2S,3R,6S,7S,8R,9S)-11-Benzenesulfonyl-2-((2R,3R)-5-methoxy-3-methyl-tetrahydro-furan-2-yl)-6,8-dimethyl-7,9-bis-triethylsilanyloxy-undecan-3-ol → (2R,3R)-2-[(1S,2R,5S,6S,7R,8S)-10-Benzenesulfonyl-2-(3,4-dimethoxy-benzyloxymethoxy)-1,5,7-trimethyl-6,8-bis-triethylsilanyloxy-decyl]-5-methoxy-3-methyl-tetrahydro-furan (188359-30-0)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1021/ja00095a072

Reference yield:

(2S,3S)-4-(benzyloxy)-3-hydroxy-N-methoxy-N,2-dimethylbutanamide (162255-08-5) → (2R,3R)-2-[(1S,2R,5S,6S,7R,8S)-10-Benzenesulfonyl-2-(3,4-dimethoxy-benzyloxymethoxy)-1,5,7-trimethyl-6,8-bis-triethylsilanyloxy-decyl]-5-methoxy-3-methyl-tetrahydro-furan (188359-30-0)

Guidance literature:

Multi-step reaction with 20 steps

1: 100 percent / imidazole / dimethylformamide / 5.5 h / 23 °C

2: 99 percent / diisobutylaluminum hydride / tetrahydrofuran; hexane / 2 h / -78 °C

3: 1.) potassium tert-butoxide / 1.) THF, room temperature, 1 h, 2.) THF, -78 -> 0 deg C

4: 97 percent / diisobutylaluminum hydride / CH₂Cl₂; hexane / 1 h / -78 °C

5: 96 percent / molecular sieves 4A, titanium tetraisopropoxide, (+)-diethyl tartrate, tert-butyl hydroperoxide / CH₂Cl₂; toluene / 1.5 h / -23 °C

6: 1.) copper(I) iodide / 1.) diethyl ether, -23 deg C, 30 min, 2.) diethyl ether, -23 -> 4 deg C

7: 100 percent / pyridine / 5 h / 0 °C

8: 91 percent / dimethylsulfoxide / 2.5 h / 50 °C

10: 100 percent / sodium, liquid ammonia / tetrahydrofuran / 0.5 h / -78 °C

11: 100 percent / imidazole / dimethylformamide / 1.3 h / 0 °C

12: 1.) NaH, 2.) Bu₄NF / 1.) DMF, mineral oil, 0 -> 23 deg C, 2.) THF, 23 deg C, 13 h

13: 1.) oxalyl chloride, DMSO, 2.) triethylamine / 1.) CH₂Cl₂, -78 deg C, 18 h, 2.) CH₂Cl₂, 0 deg C, 25 min

14: 1.) BuLi / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, -78 deg C, 3 h

15: 673 mg / NaH₂PO₄, sodium amalgam / methanol / 2 h / 0 °C

16: 98 percent / calcium, liquid ammonia / tetrahydrofuran; propan-2-ol / 1 h / -78 °C

17: 91 percent / hydrogen / Rh on alumina / ethanol / 1.6 h / 23 °C

18: 99 percent / trubutylphosphine / dimethylformamide / 14 h / 23 °C

19: 100 percent / NaHCO₃, m-chloroperoxybenzoic acid / CH₂Cl₂ / 1 h / 23 °C

20: 98 percent / diisopropylethylamine / CH₂Cl₂ / 16 h / 23 °C

With pyridine; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium dihydrogenphosphate; sodium amalgam; copper(l) iodide; n-butyllithium; oxalyl dichloride; tributylphosphine; 4 A molecular sieve; potassium tert-butylate; tetrabutyl ammonium fluoride; ammonia; hydrogen; sodium; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; calcium; dimethyl sulfoxide; (+)-Weinsaeure-diethylester; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; rhodium on alumina; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; isopropyl alcohol; toluene;

DOI:10.1021/jo9606113

Reference yield:

(E)-(4R,5S)-6-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hex-2-en-1-ol (179945-16-5) → (2R,3R)-2-[(1S,2R,5S,6S,7R,8S)-10-Benzenesulfonyl-2-(3,4-dimethoxy-benzyloxymethoxy)-1,5,7-trimethyl-6,8-bis-triethylsilanyloxy-decyl]-5-methoxy-3-methyl-tetrahydro-furan (188359-30-0)

Guidance literature:

Multi-step reaction with 16 steps

1: 96 percent / molecular sieves 4A, titanium tetraisopropoxide, (+)-diethyl tartrate, tert-butyl hydroperoxide / CH₂Cl₂; toluene / 1.5 h / -23 °C

2: 1.) copper(I) iodide / 1.) diethyl ether, -23 deg C, 30 min, 2.) diethyl ether, -23 -> 4 deg C

3: 100 percent / pyridine / 5 h / 0 °C

4: 91 percent / dimethylsulfoxide / 2.5 h / 50 °C

6: 100 percent / sodium, liquid ammonia / tetrahydrofuran / 0.5 h / -78 °C

7: 100 percent / imidazole / dimethylformamide / 1.3 h / 0 °C

8: 1.) NaH, 2.) Bu₄NF / 1.) DMF, mineral oil, 0 -> 23 deg C, 2.) THF, 23 deg C, 13 h

9: 1.) oxalyl chloride, DMSO, 2.) triethylamine / 1.) CH₂Cl₂, -78 deg C, 18 h, 2.) CH₂Cl₂, 0 deg C, 25 min

10: 1.) BuLi / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, -78 deg C, 3 h

11: 673 mg / NaH₂PO₄, sodium amalgam / methanol / 2 h / 0 °C

12: 98 percent / calcium, liquid ammonia / tetrahydrofuran; propan-2-ol / 1 h / -78 °C

13: 91 percent / hydrogen / Rh on alumina / ethanol / 1.6 h / 23 °C

14: 99 percent / trubutylphosphine / dimethylformamide / 14 h / 23 °C

15: 100 percent / NaHCO₃, m-chloroperoxybenzoic acid / CH₂Cl₂ / 1 h / 23 °C

16: 98 percent / diisopropylethylamine / CH₂Cl₂ / 16 h / 23 °C

With pyridine; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium dihydrogenphosphate; sodium amalgam; copper(l) iodide; n-butyllithium; oxalyl dichloride; tributylphosphine; 4 A molecular sieve; tetrabutyl ammonium fluoride; ammonia; hydrogen; sodium; sodium hydride; sodium hydrogencarbonate; calcium; dimethyl sulfoxide; (+)-Weinsaeure-diethylester; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; rhodium on alumina; In tetrahydrofuran; methanol; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; isopropyl alcohol; toluene;

DOI:10.1021/jo9606113

upstream raw materials:

<(3,4-dimethoxybenzyl)oxy>methyl chloride

triethylsilyl chloride

(2S,3S)-3-((2R,3R)-5-Methoxy-3-methyl-tetrahydro-furan-2-yl)-butane-1,2-diol

(2S,3R)-2-Benzyloxy-3-((2R,3R)-5-methoxy-3-methyl-tetrahydro-furan-2-yl)-butan-1-ol

Downstream raw materials:

C₇₃H₁₃₄O₁₃SSi₃

C₇₅H₁₃₆O₁₄SSi₃

[(3S,4R,5S,6S,9R,10S,11R,12R)-14-(tert-Butyl-dimethyl-silanyloxy)-4,6,10,12-tetramethyl-3,5,9,11-tetrakis-triethylsilanyloxy-tetradecane-1-sulfonyl]-benzene

(3S,4R,5S,6S,9R,10S,11R,12R)-1-Benzenesulfonyl-14-(tert-butyl-dimethyl-silanyloxy)-4,6,10,12-tetramethyl-tetradecane-3,5,9,11-tetraol