benzyl 3-deoxy-4,5-di-O-isopropylidene-7,8-di-O-benzyl-α,β-D-manno-2-octulopyranosyl fluoride

Base Information

Chemical Name:benzyl 3-deoxy-4,5-di-O-isopropylidene-7,8-di-O-benzyl-α,β-D-manno-2-octulopyranosyl fluoride
CAS No.:1032253-85-2
Molecular Formula:C₃₂H₃₅FO₇
Molecular Weight:550.624
Hs Code.:

Synonyms:benzyl 3-deoxy-4,5-di-O-isopropylidene-7,8-di-O-benzyl-α,β-D-manno-2-octulopyranosyl fluoride

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Chemical Property of benzyl 3-deoxy-4,5-di-O-isopropylidene-7,8-di-O-benzyl-α,β-D-manno-2-octulopyranosyl fluoride

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Technology Process of benzyl 3-deoxy-4,5-di-O-isopropylidene-7,8-di-O-benzyl-α,β-D-manno-2-octulopyranosyl fluoride

There total 8 articles about benzyl 3-deoxy-4,5-di-O-isopropylidene-7,8-di-O-benzyl-α,β-D-manno-2-octulopyranosyl fluoride 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: 75.0%

: benzyl 3-deoxy-4,5-di-O-isopropylidene-7,8-di-O-benzyl-α,β-D-manno-2-octulopyranosonate

: 1032253-85-2
benzyl 3-deoxy-4,5-di-O-isopropylidene-7,8-di-O-benzyl-α,β-D-manno-2-octulopyranosyl fluoride

Guidance literature:: With diethylamino-sulfur trifluoride; In dichloromethane; at -60 - 20 ℃; for 1.5h; Molecular sieve;

Reference yield: 75.0%

: benzyl 3-deoxy-4,5-di-O-isopropylidene-7,8-di-O-benzyl-α,β-D-manno-2-octulopyranosonate

: (3aR,4R,7aR)-4-((R)-1,2-Bis-benzyloxy-ethyl)-2,2-dimethyl-3a,7a-dihydro-4H-[1,3]dioxolo[4,5-c]pyran-6-carboxylic acid benzyl ester

: 1032253-85-2
benzyl 3-deoxy-4,5-di-O-isopropylidene-7,8-di-O-benzyl-α,β-D-manno-2-octulopyranosyl fluoride

Guidance literature:: With 4 A molecular sieve; 4,4'-diaminostilbene-2,2'-disulfonic acid; In dichloromethane; at -60 - 20 ℃;
DOI:10.1002/chem.200701165

Reference yield:

: C₁₂H₂₀O₆

: 1032253-85-2
benzyl 3-deoxy-4,5-di-O-isopropylidene-7,8-di-O-benzyl-α,β-D-manno-2-octulopyranosyl fluoride

Guidance literature:: Multi-step reaction with 7 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h

1.2: 10 h / 0 °C

2.1: palladium on activated charcoal / methanol / 10 h / Reflux

2.2: 0.5 h / 0 °C

3.1: sodium tetrahydroborate / ethanol / 10 h

4.1: thionyl chloride; triethylamine / dichloromethane / 0.5 h / -15 °C

4.2: 0.33 h

5.1: n-butyllithium / tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide / 2 h

5.2: 2 h / 20 °C

6.1: N-Bromosuccinimide; sodium hydrogencarbonate / water; acetone / 0.17 h / 0 °C

7.1: diethylamino-sulfur trifluoride / dichloromethane / 1.5 h / -60 - 20 °C / Molecular sieve

With sodium tetrahydroborate; N-Bromosuccinimide; n-butyllithium; thionyl chloride; diethylamino-sulfur trifluoride; palladium on activated charcoal; sodium hydride; sodium hydrogencarbonate; triethylamine; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; mineral oil;