methyl 2,3-di-O-benzyl-L-glycero-β-D-manno-heptopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside

Base Information

Chemical Name:methyl 2,3-di-O-benzyl-L-glycero-β-D-manno-heptopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside
CAS No.:850648-03-2
Molecular Formula:C₄₉H₅₆O₁₂
Molecular Weight:836.976
Hs Code.:

Synonyms:methyl 2,3-di-O-benzyl-L-glycero-β-D-manno-heptopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside

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Chemical Property of methyl 2,3-di-O-benzyl-L-glycero-β-D-manno-heptopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside

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Technology Process of methyl 2,3-di-O-benzyl-L-glycero-β-D-manno-heptopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside

There total 13 articles about methyl 2,3-di-O-benzyl-L-glycero-β-D-manno-heptopyranosyl-(1->4)-2,3,6-tri-O-benzyl-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: 75.0%

: 850647-96-0
methyl 2,3-di-O-benzyl-4,6-O-(p-methoxybenzylidene)-7-O-(t-butyldiphenylsilyl)-L-glycero-β-D-manno-heptopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside

: 850648-03-2
methyl 2,3-di-O-benzyl-L-glycero-β-D-manno-heptopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside

Guidance literature:: methyl 2,3-di-O-benzyl-4,6-O-(p-methoxybenzylidene)-7-O-(t-butyldiphenylsilyl)-L-glycero-β-D-manno-heptopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside; With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 3h;

With camphor-10-sulfonic acid; In methanol; for 1h; Heating;
DOI:10.1021/ja061594u

Reference yield:

: 850647-87-9
phenyl 2,3-di-O-benzyl-6,7-dideoxy-4-O-(p-methoxybenzyl)-α-D-thiohept-6-enopyranoside

: 850648-03-2
methyl 2,3-di-O-benzyl-L-glycero-β-D-manno-heptopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1.1: 61 percent / NMNO; OsO₄ / 2-methyl-propan-2-ol / 4 h / 20 °C

2.1: imidazole / CH₂Cl₂ / 2 h / 0 - 10 °C

2.2: 92 percent / PPh₃; DIAD / tetrahydrofuran / 5 h / 20 °C

3.1: 95 percent / K₂CO₃ / methanol; CH₂Cl₂ / 3 h / 20 °C

4.1: DDQ / CH₂Cl₂; H₂O / 2 h / 20 °C

5.1: 1-benzenesulfinyl piperidine; 2,4,6-tri-tert-butylpyrimidine; Tf₂O / CH₂Cl₂ / 0.33 h / -60 °C

5.2: CH₂Cl₂ / 1 h / -60 °C

6.1: TBAF / tetrahydrofuran / 3 h / 20 °C

6.2: 75 percent / CSA / methanol / 1 h / Heating

With 1H-imidazole; osmium(VIII) oxide; 1-benzenesulfinyl piperidine; bis-(2-chloro-ethyl)-methyl-amine oxide; trifluoromethylsulfonic anhydride; tetrabutyl ammonium fluoride; potassium carbonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; 2,4,6-tri-tert-butylpyrimidine; In tetrahydrofuran; methanol; dichloromethane; water; tert-butyl alcohol;
DOI:10.1021/ja061594u

Reference yield:

: 850647-86-8
phenyl 2,3-di-O-benzyl-4-O-(p-methoxybenzyl)-α-D-thiomannopyranoside

: 850648-03-2
methyl 2,3-di-O-benzyl-L-glycero-β-D-manno-heptopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1.1: oxalyl chloride; DMSO / CH₂Cl₂ / 1 h / -50 °C

1.2: 65 percent / nBuLi / tetrahydrofuran; hexane / 1 h / -40 °C

2.1: 61 percent / NMNO; OsO₄ / 2-methyl-propan-2-ol / 4 h / 20 °C

3.1: imidazole / CH₂Cl₂ / 2 h / 0 - 10 °C

3.2: 92 percent / PPh₃; DIAD / tetrahydrofuran / 5 h / 20 °C

4.1: 95 percent / K₂CO₃ / methanol; CH₂Cl₂ / 3 h / 20 °C

5.1: DDQ / CH₂Cl₂; H₂O / 2 h / 20 °C

6.1: 1-benzenesulfinyl piperidine; 2,4,6-tri-tert-butylpyrimidine; Tf₂O / CH₂Cl₂ / 0.33 h / -60 °C

6.2: CH₂Cl₂ / 1 h / -60 °C

7.1: TBAF / tetrahydrofuran / 3 h / 20 °C

7.2: 75 percent / CSA / methanol / 1 h / Heating

With 1H-imidazole; osmium(VIII) oxide; oxalyl dichloride; 1-benzenesulfinyl piperidine; bis-(2-chloro-ethyl)-methyl-amine oxide; trifluoromethylsulfonic anhydride; tetrabutyl ammonium fluoride; potassium carbonate; dimethyl sulfoxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; 2,4,6-tri-tert-butylpyrimidine; In tetrahydrofuran; methanol; dichloromethane; water; tert-butyl alcohol;
DOI:10.1021/ja061594u