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

Base Information

Chemical Name: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
CAS No.:850647-97-1
Molecular Formula:C₅₅H₆₆O₁₂Si
Molecular Weight:947.207
Hs Code.:

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

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 9 articles about 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 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%

: 850647-93-7
phenyl 2,3-di-O-benzyl-4,6-O-(p-methoxybenzylidene)-7-O-(tert-butyldiphenylsilyl)-D-glycero-α-D-thiomannoheptopyranoside

: 14133-63-2
methyl 2,3-O-isopropylidene-α-L-rhamnoside

: 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

Guidance literature:: phenyl 2,3-di-O-benzyl-4,6-O-(p-methoxybenzylidene)-7-O-(tert-butyldiphenylsilyl)-D-glycero-α-D-thiomannoheptopyranoside; With sulfobromophthalein sodium; In dichloromethane; at -60 ℃; for 0.25h;

methyl 2,3-O-isopropylidene-α-L-rhamnoside; With trifluoromethylsulfonic anhydride; In dichloromethane; at -60 - 20 ℃; for 4h;
DOI:10.1021/ol050224s

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 4 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

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

Reference yield:

: 850647-89-1
phenyl 2,3-di-O-benzyl-4-O-(p-methoxybenzyl)-D-glycero-α-D-thio-manno-heptopyranoside

: 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

Guidance literature:: Multi-step reaction with 3 steps

1.1: 87 percent / DDQ / CH₂Cl₂; H₂O / 1 h / 20 °C

2.1: 98 percent / imidazole / CH₂Cl₂ / 2 h / 0 - 10 °C

3.1: 1-benzenesulfinyl piperidine; 2,4,6-tri-tert-butylpyrimidine; Tf₂O / CH₂Cl₂ / 0.33 h / -60 °C

3.2: 88 percent / CH₂Cl₂ / 1 h / -60 °C

With 1H-imidazole; 1-benzenesulfinyl piperidine; trifluoromethylsulfonic anhydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; 2,4,6-tri-tert-butylpyrimidine; In dichloromethane; water;
DOI:10.1021/ja061594u