thioethyl 2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-6-O-p-methoxybenzyl-β-D-glucopyranoside

Base Information

Chemical Name:thioethyl 2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-6-O-p-methoxybenzyl-β-D-glucopyranoside
CAS No.:765910-34-7
Molecular Formula:C₃₅H₄₀O₉S
Molecular Weight:636.763
Hs Code.:

Synonyms:thioethyl 2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-6-O-p-methoxybenzyl-β-D-glucopyranoside

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Chemical Property of thioethyl 2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-6-O-p-methoxybenzyl-β-D-glucopyranoside

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Technology Process of thioethyl 2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-6-O-p-methoxybenzyl-β-D-glucopyranoside

There total 2 articles about thioethyl 2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-6-O-p-methoxybenzyl-β-D-glucopyranoside 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: 88.0%

: 123-76-2
levulinic acid

: Benzoic acid (2S,3R,4S,5R,6R)-4-benzyloxy-2-ethylsulfanyl-5-hydroxy-6-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-yl ester

: 765910-34-7
thioethyl 2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-6-O-p-methoxybenzyl-β-D-glucopyranoside

Guidance literature:: With dmap; diisopropyl-carbodiimide; In dichloromethane; at 0 - 20 ℃; Inert atmosphere; Darkness;
DOI:10.1002/adsc.201000008

Reference yield:

: thioethyl 2-O-benzoyl-3-O-benzyl-4,6-di-O-p-methoxybenzylidene-β-D-glucopyranoside

: 765910-34-7
thioethyl 2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-6-O-p-methoxybenzyl-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: NaCNBH₃; 4 Angstroem molecular sieves; TFA / dimethylformamide / 14 h / 0 - 20 °C

2: 115 mg / DMAP; diisopropylcarbodiimide / CH₂Cl₂ / 13 h / 0 - 20 °C

With dmap; 4 A molecular sieve; sodium cyanoborohydride; trifluoroacetic acid; diisopropyl-carbodiimide; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2004.06.037

Reference yield:

: 765910-32-5
allyl 4-O-acetyl-6-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranoside

: 765910-34-7
thioethyl 2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-6-O-p-methoxybenzyl-β-D-glucopyranoside

: Benzoic acid (2R,3R,4S,5R,6R)-2-[(2R,3S,4R,5R,6R)-3-acetoxy-6-allyloxy-2-benzyloxymethyl-5-(2,2,2-trichloro-acetylamino)-tetrahydro-pyran-4-yloxy]-4-benzyloxy-6-(4-methoxy-benzyloxymethyl)-5-(4-oxo-pentanoyloxy)-tetrahydro-pyran-3-yl ester

Guidance literature:: With 4 A molecular sieve; methyl trifluoromethanesulfonate; In dichloromethane; at -25 - 20 ℃; for 14h;
DOI:10.1016/j.tet.2004.06.037