9-[4-benzyloxy-3-[[4-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-2-ethylsulfanyl-tetrahydro-furan-3-yloxy]-(4-methoxy-phenyl)-methoxy]-5-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-furan-2-yloxy]-nonanoic acid methyl ester

Base Information

• Chemical Name: 9-[4-benzyloxy-3-[[4-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-2-ethylsulfanyl-tetrahydro-furan-3-yloxy]-(4-methoxy-phenyl)-methoxy]-5-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-furan-2-yloxy]-nonanoic acid methyl ester
• CAS No.: 282107-58-8
• Molecular Formula: C₆₅H₈₆O₁₃SSi
• Molecular Weight: 1135.54
• Mol file: 282107-58-8.mol

Synonyms:9-[4-benzyloxy-3-[[4-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-2-ethylsulfanyl-tetrahydro-furan-3-yloxy]-(4-methoxy-phenyl)-methoxy]-5-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-furan-2-yloxy]-nonanoic acid methyl ester

Chemical Property of 9-[4-benzyloxy-3-[[4-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-2-ethylsulfanyl-tetrahydro-furan-3-yloxy]-(4-methoxy-phenyl)-methoxy]-5-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-furan-2-yloxy]-nonanoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 9-[4-benzyloxy-3-[[4-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-2-ethylsulfanyl-tetrahydro-furan-3-yloxy]-(4-methoxy-phenyl)-methoxy]-5-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-furan-2-yloxy]-nonanoic acid methyl ester

There total 14 articles about 9-[4-benzyloxy-3-[[4-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-2-ethylsulfanyl-tetrahydro-furan-3-yloxy]-(4-methoxy-phenyl)-methoxy]-5-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-furan-2-yloxy]-nonanoic acid methyl 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: 84.0%

8-methoxycarbonyloctyl 3-O-benzyl-5-O-pivaloyl-α-D-arabinofuranoside (282107-55-5) + ethyl 3-O-benzyl-5-O-tert-butyldiphenylsilyl-2-O-(4-methoxybenzyl)-1-thio-α-D-arabinofuranoside (282107-57-7) → 9-[4-benzyloxy-3-[[4-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-2-ethylsulfanyl-tetrahydro-furan-3-yloxy]-(4-methoxy-phenyl)-methoxy]-5-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-furan-2-yloxy]-nonanoic acid methyl ester (282107-58-8)

Guidance literature:

With 4 A molecular sieve; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; at 0 - 20 ℃; for 2.5h;

DOI:10.1039/b000873g

Reference yield:

benzyl bromide (100-39-0) → 9-[4-benzyloxy-3-[[4-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-2-ethylsulfanyl-tetrahydro-furan-3-yloxy]-(4-methoxy-phenyl)-methoxy]-5-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-furan-2-yloxy]-nonanoic acid methyl ester (282107-58-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 90 percent / NaH / dimethylformamide / 1 h / 20 °C

2: SnCl₄; 4 Angstroem molecular sieves / CH₂Cl₂ / 3 h / 20 °C

3: 60 percent / MeONa / methanol / 1 h / 20 °C

4: 80 percent / DMAP; pyridine / 1.5 h / 0 °C

5: 84 percent / DDQ; 4 Angstroem molecular sieves / CH₂Cl₂ / 2.5 h / 0 - 20 °C

With pyridine; dmap; 4 A molecular sieve; sodium methylate; tin(IV) chloride; sodium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In methanol; dichloromethane; N,N-dimethyl-formamide; 1: Etherification / 2: Ring cleavage / 3: Deacylation / 4: Acylation / 5: Condensation;

DOI:10.1039/b000873g

Reference yield:

(1R,3S,7S,8R)-5-Dichloromethyl-2,4,6,10-tetraoxa-tricyclo[3.3.2.03,7]decan-8-ol → 9-[4-benzyloxy-3-[[4-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-2-ethylsulfanyl-tetrahydro-furan-3-yloxy]-(4-methoxy-phenyl)-methoxy]-5-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-furan-2-yloxy]-nonanoic acid methyl ester (282107-58-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 90 percent / NaH / dimethylformamide / 1 h / 20 °C

2: SnCl₄; 4 Angstroem molecular sieves / CH₂Cl₂ / 3 h / 20 °C

3: 60 percent / MeONa / methanol / 1 h / 20 °C

4: 80 percent / DMAP; pyridine / 1.5 h / 0 °C

5: 84 percent / DDQ; 4 Angstroem molecular sieves / CH₂Cl₂ / 2.5 h / 0 - 20 °C

With pyridine; dmap; 4 A molecular sieve; sodium methylate; tin(IV) chloride; sodium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In methanol; dichloromethane; N,N-dimethyl-formamide; 1: Etherification / 2: Ring cleavage / 3: Deacylation / 4: Acylation / 5: Condensation;

DOI:10.1039/b000873g

upstream raw materials:

8-methoxycarbonyloctyl 3-O-benzyl-5-O-pivaloyl-α-D-arabinofuranoside

ethyl 3-O-benzyl-5-O-tert-butyldiphenylsilyl-2-O-(4-methoxybenzyl)-1-thio-α-D-arabinofuranoside

methyl 9-hydroxynonanoate

pivaloyl chloride

Downstream raw materials:

9-[(2S,3S,4R,5R)-3-[(2S,3S,4R,5R)-3-Acetoxy-4-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yloxy]-4-benzyloxy-5-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-furan-2-yloxy]-nonanoic acid methyl ester

8-(methoxycarbonyl)octyl 2-O-(2-O-acetyl-3-O-benzyl)-β-D-arabinofuranosyl)-3-O-benzyl-5-O-pivaloyl-α-D-arabinofuranoside

8-(methoxycarbonyl)octyl 2-O-(3-O-benzyl-5-O-tert-butyldiphenylsilyl)-β-D-arabinofuranosyl)-3-O-benzyl-5-O-pivaloyl-α-D-arabinofuranoside