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

Base Information

Chemical Name:8-(methoxycarbonyl)octyl 2-O-(2-O-acetyl-3-O-benzyl)-β-D-arabinofuranosyl)-3-O-benzyl-5-O-pivaloyl-α-D-arabinofuranoside
CAS No.:282107-60-2
Molecular Formula:C₄₁H₅₈O₁₃
Molecular Weight:758.904
Hs Code.:

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

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

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

There total 15 articles about 8-(methoxycarbonyl)octyl 2-O-(2-O-acetyl-3-O-benzyl)-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: 76.0%

: 628686-53-3
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

: 282107-60-2
8-(methoxycarbonyl)octyl 2-O-(2-O-acetyl-3-O-benzyl)-β-D-arabinofuranosyl)-3-O-benzyl-5-O-pivaloyl-α-D-arabinofuranoside

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 1h;
DOI:10.1002/ejoc.200300303

Reference yield:

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

: 282107-60-2
8-(methoxycarbonyl)octyl 2-O-(2-O-acetyl-3-O-benzyl)-β-D-arabinofuranosyl)-3-O-benzyl-5-O-pivaloyl-α-D-arabinofuranoside

Guidance literature:: Multi-step reaction with 2 steps

1: 99 percent / pyridine / ethyl acetate

2: 76 percent / Bu₄NF / tetrahydrofuran / 1 h / 20 °C

With pyridine; tetrabutyl ammonium fluoride; In tetrahydrofuran; ethyl acetate;
DOI:10.1002/ejoc.200300303

Reference yield:

: 100-39-0
benzyl bromide

: 282107-60-2
8-(methoxycarbonyl)octyl 2-O-(2-O-acetyl-3-O-benzyl)-β-D-arabinofuranosyl)-3-O-benzyl-5-O-pivaloyl-α-D-arabinofuranoside

Guidance literature:: Multi-step reaction with 8 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

7: pyridine / CH₂Cl₂ / 20 °C

8: n-Bu₄NF / tetrahydrofuran / 0.5 h / 20 °C

With pyridine; dmap; iodonium di(2,4,6-trimethylpyridine) perchlorate; 4 A molecular sieve; tetrabutyl ammonium fluoride; sodium methylate; tin(IV) chloride; sodium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 1: Etherification / 2: Ring cleavage / 3: Deacylation / 4: Acylation / 5: Condensation / 6: Intramolecular glycosylation / 7: Acetylation / 8: Desilylation;
DOI:10.1039/b000873g