methyl 6-O-benzyl-2-O-(11,14-dioxo-3,6-dioxa-9-thiapentadecyl)-α-D-glucopyranoside

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Chemical Name:methyl 6-O-benzyl-2-O-(11,14-dioxo-3,6-dioxa-9-thiapentadecyl)-α-D-glucopyranoside
CAS No.:245047-80-7
Molecular Formula:C₂₆H₄₀O₁₀S
Molecular Weight:544.664
Hs Code.:

Synonyms:methyl 6-O-benzyl-2-O-(11,14-dioxo-3,6-dioxa-9-thiapentadecyl)-α-D-glucopyranoside

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Chemical Property of methyl 6-O-benzyl-2-O-(11,14-dioxo-3,6-dioxa-9-thiapentadecyl)-α-D-glucopyranoside

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Technology Process of methyl 6-O-benzyl-2-O-(11,14-dioxo-3,6-dioxa-9-thiapentadecyl)-α-D-glucopyranoside

There total 8 articles about methyl 6-O-benzyl-2-O-(11,14-dioxo-3,6-dioxa-9-thiapentadecyl)-α-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: 93.0%

: 152757-44-3
1-bromohexane-2,5-dione

: 245047-78-3
methyl 6-O-benzyl-2-O-(8-sulfanyl-3,6-dioxaoctyl)-α-D-glucopyranoside

: 245047-80-7
methyl 6-O-benzyl-2-O-(11,14-dioxo-3,6-dioxa-9-thiapentadecyl)-α-D-glucopyranoside

Guidance literature:: With caesium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 0.333333h;
DOI:10.3891/acta.chem.scand.53-0480

Reference yield:

: 20839-38-7,23392-30-5,23392-33-8,63864-93-7,65309-96-8,65309-99-1,67393-10-6,82264-32-2,23392-32-7
methyl 6-O-benzyl-α-D-glucopyranoside

: 245047-80-7
methyl 6-O-benzyl-2-O-(11,14-dioxo-3,6-dioxa-9-thiapentadecyl)-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1.1: NaH / dimethylformamide / 15.5 h / 45 - 95 °C

2.1: 4-dimethylaminopyridine / pyridine / 20 °C

3.1: 90 percent / Bu₄NF*3H₂O / tetrahydrofuran / 3 h / 0 °C

4.1: 77 percent / 4-dimethylaminopyridine / pyridine / 36 h / 0 - 4 °C

5.1: 83 percent / NaOMe / methanol / 6 h / 20 °C

6.1: Na₂S₂O₃*3H₂O / H₂O; ethanol / 8 h / 85 °C

6.2: 81 percent / cysteamine hydrochloride / H₂O / 14 h / 20 °C

7.1: 93 percent / Cs₂CO₃ / dimethylformamide / 0.33 h / 20 °C

With dmap; tetrabutyl ammonium fluoride; sodium methylate; sodium hydride; caesium carbonate; sodium thiosulfate; In tetrahydrofuran; pyridine; methanol; ethanol; water; N,N-dimethyl-formamide; 1.1: Alkylation / 2.1: Acetylation / 3.1: Hydrolysis / 4.1: Esterification / 5.1: Deacetylation / 6.1: Hydrolysis / 6.2: Substitution / 7.1: Substitution;
DOI:10.3891/acta.chem.scand.53-0480

Reference yield:

: 199484-66-7
toluene-4-sulfonic acid 2-{2-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-ethoxy}-ethyl ester

: 245047-80-7
methyl 6-O-benzyl-2-O-(11,14-dioxo-3,6-dioxa-9-thiapentadecyl)-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1.1: NaH / dimethylformamide / 15.5 h / 45 - 95 °C

2.1: 4-dimethylaminopyridine / pyridine / 20 °C

3.1: 90 percent / Bu₄NF*3H₂O / tetrahydrofuran / 3 h / 0 °C

4.1: 77 percent / 4-dimethylaminopyridine / pyridine / 36 h / 0 - 4 °C

5.1: 83 percent / NaOMe / methanol / 6 h / 20 °C

6.1: Na₂S₂O₃*3H₂O / H₂O; ethanol / 8 h / 85 °C

6.2: 81 percent / cysteamine hydrochloride / H₂O / 14 h / 20 °C

7.1: 93 percent / Cs₂CO₃ / dimethylformamide / 0.33 h / 20 °C

With dmap; tetrabutyl ammonium fluoride; sodium methylate; sodium hydride; caesium carbonate; sodium thiosulfate; In tetrahydrofuran; pyridine; methanol; ethanol; water; N,N-dimethyl-formamide; 1.1: Alkylation / 2.1: Acetylation / 3.1: Hydrolysis / 4.1: Esterification / 5.1: Deacetylation / 6.1: Hydrolysis / 6.2: Substitution / 7.1: Substitution;
DOI:10.3891/acta.chem.scand.53-0480