3-O-(2,3,4-tri-O-benzyl-6-deoxy-6-thioacetyl-α-D-glucopyranosyl)-1-O-palmitoyl-glycerol

Base Information

Chemical Name:3-O-(2,3,4-tri-O-benzyl-6-deoxy-6-thioacetyl-α-D-glucopyranosyl)-1-O-palmitoyl-glycerol
CAS No.:267900-45-8
Molecular Formula:C₄₈H₆₈O₉S
Molecular Weight:821.129
Hs Code.:

Synonyms:3-O-(2,3,4-tri-O-benzyl-6-deoxy-6-thioacetyl-α-D-glucopyranosyl)-1-O-palmitoyl-glycerol

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Chemical Property of 3-O-(2,3,4-tri-O-benzyl-6-deoxy-6-thioacetyl-α-D-glucopyranosyl)-1-O-palmitoyl-glycerol

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Technology Process of 3-O-(2,3,4-tri-O-benzyl-6-deoxy-6-thioacetyl-α-D-glucopyranosyl)-1-O-palmitoyl-glycerol

There total 7 articles about 3-O-(2,3,4-tri-O-benzyl-6-deoxy-6-thioacetyl-α-D-glucopyranosyl)-1-O-palmitoyl-glycerol 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: 40.5%

: 57-10-3
1-hexadecylcarboxylic acid

: 265312-95-6
3-O-(2,3,4-tri-O-benzyl-6-deoxy-6-thioacetyl-α-D-glucopyranosyl)-glycerol

: 267900-45-8
3-O-(2,3,4-tri-O-benzyl-6-deoxy-6-thioacetyl-α-D-glucopyranosyl)-1-O-palmitoyl-glycerol

: 267900-43-6
3-O-(2,3,4-tri-O-benzyl-6-deoxy-6-thioacetyl-α-D-glucopyranosyl)-1,2-di-O-palmitoyl-glycerol

Guidance literature:: With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20 ℃; for 16h;
DOI:10.1016/S0968-0896(00)00252-2

Reference yield:

: 78184-40-4
1-O-allyl-2,3,4-tri-O-benzyl-α-D-glucopyranoside

: 267900-45-8
3-O-(2,3,4-tri-O-benzyl-6-deoxy-6-thioacetyl-α-D-glucopyranosyl)-1-O-palmitoyl-glycerol

Guidance literature:: Multi-step reaction with 4 steps

1: 72 percent / DMAP / pyridine / 20 h / 20 °C

2: 88 percent / ethanol / 3 h / Heating

3: 57 percent / OsO₄; trimethylamine N-oxide / 2-methyl-propan-2-ol; H₂O / 30 h / 20 °C

4: 32.3 percent / EDCI; DMAP / CH₂Cl₂ / 16 h / 20 °C

With dmap; osmium(VIII) oxide; trimethylamine-N-oxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In pyridine; ethanol; dichloromethane; water; tert-butyl alcohol; 1: tosylation / 2: substitution / 3: oxidation / 4: esterification;
DOI:10.1016/S0968-0896(00)00252-2

Reference yield:

: 100-39-0
benzyl bromide

: 267900-45-8
3-O-(2,3,4-tri-O-benzyl-6-deoxy-6-thioacetyl-α-D-glucopyranosyl)-1-O-palmitoyl-glycerol

Guidance literature:: Multi-step reaction with 6 steps

1: 68.2 percent / NaH / dimethylformamide

2: LiAlH₄; AlCl₃ / diethyl ether; CH₂Cl₂ / 2 h / Heating

3: 72 percent / DMAP / pyridine / 20 h / 20 °C

4: 88 percent / ethanol / 3 h / Heating

5: 57 percent / OsO₄; trimethylamine N-oxide / 2-methyl-propan-2-ol; H₂O / 30 h / 20 °C

6: 32.3 percent / EDCI; DMAP / CH₂Cl₂ / 16 h / 20 °C

With dmap; osmium(VIII) oxide; lithium aluminium tetrahydride; aluminium trichloride; trimethylamine-N-oxide; sodium hydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In pyridine; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 1: etherification / 2: reductive cleavage / 3: tosylation / 4: substitution / 5: oxidation / 6: esterification;
DOI:10.1016/S0968-0896(00)00252-2