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

Base Information

Chemical Name:methyl 2,3-di-O-benzyl-D-glycero-β-D-manno-heptopyranosyl-(1->4)-α-L-rhamnopyranoside
CAS No.:850648-05-4
Molecular Formula:C₂₈H₃₈O₁₁
Molecular Weight:550.603
Hs Code.:

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

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

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

There total 11 articles about methyl 2,3-di-O-benzyl-D-glycero-β-D-manno-heptopyranosyl-(1->4)-α-L-rhamnopyranoside 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: 72.0%

: 850647-97-1
methyl 2,3-di-O-benzyl-4,6-O-(p-methoxybenzylidene)-7-O-(t-butyldiphenylsilyl)-D-glycero-β-D-manno-heptopyranosyl-(1->4)-2,3-O-isopropylidene-α-L-rhamnopyranoside

: 850648-05-4
methyl 2,3-di-O-benzyl-D-glycero-β-D-manno-heptopyranosyl-(1->4)-α-L-rhamnopyranoside

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

With camphor-10-sulfonic acid; In methanol; for 3h; Heating;
DOI:10.1021/ja061594u

Reference yield:

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

: 850648-05-4
methyl 2,3-di-O-benzyl-D-glycero-β-D-manno-heptopyranosyl-(1->4)-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 6 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: 87 percent / DDQ / CH₂Cl₂; H₂O / 1 h / 20 °C

4.1: 98 percent / imidazole / CH₂Cl₂ / 2 h / 0 - 10 °C

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

5.2: 88 percent / CH₂Cl₂ / 1 h / -60 °C

6.1: TBAF / tetrahydrofuran / 2 h / 20 °C

6.2: 72 percent / CSA / methanol / 3 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; dimethyl sulfoxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; 2,4,6-tri-tert-butylpyrimidine; In tetrahydrofuran; dichloromethane; water; tert-butyl alcohol;
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

: 850648-05-4
methyl 2,3-di-O-benzyl-D-glycero-β-D-manno-heptopyranosyl-(1->4)-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 5 steps

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

2.1: 87 percent / DDQ / CH₂Cl₂; H₂O / 1 h / 20 °C

3.1: 98 percent / imidazole / CH₂Cl₂ / 2 h / 0 - 10 °C

4.1: 1-benzenesulfinyl piperidine; 2,4,6-tri-tert-butylpyrimidine; Tf₂O / CH₂Cl₂ / 0.33 h / -60 °C

4.2: 88 percent / CH₂Cl₂ / 1 h / -60 °C

5.1: TBAF / tetrahydrofuran / 2 h / 20 °C

5.2: 72 percent / CSA / methanol / 3 h / Heating

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