methyl 4-O-[4,6-O-benzylidene-2-O-(prop-2-ynyl)-3-O-tert-butyldimethylsilyl-β-D-mannopyranosyl]-(1->4)-2,3-O-isopropylidene-α-L-rhamnopyranoside

Base Information

Chemical Name:methyl 4-O-[4,6-O-benzylidene-2-O-(prop-2-ynyl)-3-O-tert-butyldimethylsilyl-β-D-mannopyranosyl]-(1->4)-2,3-O-isopropylidene-α-L-rhamnopyranoside
CAS No.:855306-38-6
Molecular Formula:C₃₂H₄₈O₁₀Si
Molecular Weight:620.813
Hs Code.:

Synonyms:methyl 4-O-[4,6-O-benzylidene-2-O-(prop-2-ynyl)-3-O-tert-butyldimethylsilyl-β-D-mannopyranosyl]-(1->4)-2,3-O-isopropylidene-α-L-rhamnopyranoside

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Chemical Property of methyl 4-O-[4,6-O-benzylidene-2-O-(prop-2-ynyl)-3-O-tert-butyldimethylsilyl-β-D-mannopyranosyl]-(1->4)-2,3-O-isopropylidene-α-L-rhamnopyranoside

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Technology Process of methyl 4-O-[4,6-O-benzylidene-2-O-(prop-2-ynyl)-3-O-tert-butyldimethylsilyl-β-D-mannopyranosyl]-(1->4)-2,3-O-isopropylidene-α-L-rhamnopyranoside

There total 4 articles about methyl 4-O-[4,6-O-benzylidene-2-O-(prop-2-ynyl)-3-O-tert-butyldimethylsilyl-β-D-mannopyranosyl]-(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: 95.0%

: 855306-34-2
phenyl 4,6-O-benzylidene-2-O-(prop-2-ynyl)-3-O-(tert-butyldimethylsilyl)-1-thio-α-D-mannopyranoside

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

: 855306-38-6
methyl 4-O-[4,6-O-benzylidene-2-O-(prop-2-ynyl)-3-O-tert-butyldimethylsilyl-β-D-mannopyranosyl]-(1->4)-2,3-O-isopropylidene-α-L-rhamnopyranoside

Guidance literature:: phenyl 4,6-O-benzylidene-2-O-(prop-2-ynyl)-3-O-(tert-butyldimethylsilyl)-1-thio-α-D-mannopyranoside; With 1-benzenesulfinyl piperidine; trifluoromethylsulfonic anhydride; 2,4,6-tri-tert-butylpyrimidine; 4 A molecular sieve; In dichloromethane; at -60 ℃; for 0.5h;

methyl 2,3-O-isopropylidene-α-L-rhamnoside; In dichloromethane; at -60 ℃; for 2h;
DOI:10.1021/ol050680g

Reference yield:

: 855306-33-1
phenyl 4,6-O-benzylidene-2-O-(prop-2-ynyl)-1-thio-α-D-mannopyranoside

: 855306-38-6
methyl 4-O-[4,6-O-benzylidene-2-O-(prop-2-ynyl)-3-O-tert-butyldimethylsilyl-β-D-mannopyranosyl]-(1->4)-2,3-O-isopropylidene-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1.1: 92 percent / imidazole / dimethylformamide / 12 h / 20 °C

2.1: 1-benzenesulfinyl piperidine; 2,4,6-tri-tert-butylpyrimidine; trifluoromethanesulfonic anhydride / CH₂Cl₂ / 0.5 h / -60 °C

2.2: 95 percent / CH₂Cl₂ / 2 h / -60 °C

With 1H-imidazole; 1-benzenesulfinyl piperidine; trifluoromethanesulfonic acid anhydride; 2,4,6-tri-tert-butylpyrimidine; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo0526789

Reference yield:

: 855306-32-0
phenyl 4,6-O-benzylidene-2-O-(prop-2-ynyl)-3-O-p-methoxybenzyl-1-thio-α-D-mannopyranoside

: 855306-38-6
methyl 4-O-[4,6-O-benzylidene-2-O-(prop-2-ynyl)-3-O-tert-butyldimethylsilyl-β-D-mannopyranosyl]-(1->4)-2,3-O-isopropylidene-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: 93 percent / DDQ / CH₂Cl₂; H₂O / 3 h / 20 °C

2.1: 92 percent / imidazole / dimethylformamide / 12 h / 20 °C

3.1: 1-benzenesulfinyl piperidine; 2,4,6-tri-tert-butylpyrimidine; trifluoromethanesulfonic anhydride / CH₂Cl₂ / 0.5 h / -60 °C

3.2: 95 percent / CH₂Cl₂ / 2 h / -60 °C

With 1H-imidazole; 1-benzenesulfinyl piperidine; trifluoromethanesulfonic acid anhydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; 2,4,6-tri-tert-butylpyrimidine; In dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jo0526789