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

Base Information

• Chemical Name: 8-(methoxycarbonyl)octyl 2-O-(3-O-benzyl-5-O-tert-butyldiphenylsilyl)-β-D-arabinofuranosyl)-3-O-benzyl-5-O-pivaloyl-α-D-arabinofuranoside
• CAS No.: 282107-59-9
• Molecular Formula: C₅₅H₇₄O₁₂Si
• Molecular Weight: 955.271
• Mol file: 282107-59-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 16 articles about 8-(methoxycarbonyl)octyl 2-O-(3-O-benzyl-5-O-tert-butyldiphenylsilyl)-β-D-arabinofuranosyl)-3-O-benzyl-5-O-pivaloyl-α-D-arabinofuranoside 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: 73.0%

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) → 8-(methoxycarbonyl)octyl 2-O-(3-O-benzyl-5-O-tert-butyldiphenylsilyl)-β-D-arabinofuranosyl)-3-O-benzyl-5-O-pivaloyl-α-D-arabinofuranoside (282107-59-9)

Guidance literature:

With iodonium di(2,4,6-trimethylpyridine) perchlorate; 4 A molecular sieve; In dichloromethane; at 20 ℃; for 1.5h;

DOI:10.1039/b000873g

Reference yield: 63.0%

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) → 8-(methoxycarbonyl)octyl 2-O-(3-O-benzyl-5-O-tert-butyldiphenylsilyl)-β-D-arabinofuranosyl)-3-O-benzyl-5-O-pivaloyl-α-D-arabinofuranoside (282107-59-9)

Guidance literature:

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

With iodonium(di-γ-collidine) perchlorate; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1002/ejoc.200300303

Reference yield:

benzyl bromide (100-39-0) → 8-(methoxycarbonyl)octyl 2-O-(3-O-benzyl-5-O-tert-butyldiphenylsilyl)-β-D-arabinofuranosyl)-3-O-benzyl-5-O-pivaloyl-α-D-arabinofuranoside (282107-59-9)

Guidance literature:

Multi-step reaction with 6 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

6: 73 percent / iodonium dicollidine perchlorate; 4 Angstroem molecular sieves / CH₂Cl₂ / 1.5 h / 20 °C

With pyridine; dmap; iodonium di(2,4,6-trimethylpyridine) perchlorate; 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 / 6: Intramolecular glycosylation;

DOI:10.1039/b000873g

upstream raw materials:

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

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

Downstream raw materials:

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

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