methyl 4-O-[4,6-O-benzylidene-2-O-(prop-2-ynyl)-3-O-benzyl-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-benzyl-β-D-mannopyranosyl]-(1->4)-2,3-O-isopropylidene-α-L-rhamnopyranoside
CAS No.:887471-17-2
Molecular Formula:C₃₃H₄₀O₁₀
Molecular Weight:596.675
Hs Code.:

Synonyms:methyl 4-O-[4,6-O-benzylidene-2-O-(prop-2-ynyl)-3-O-benzyl-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-benzyl-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-benzyl-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-benzyl-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:

: 887471-11-6
phenyl 4,6-O-benzylidene-3-O-benzyl-2-O-(prop-2-ynyl)-1-thio-α-D-mannopyranoside

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

: 887471-17-2
methyl 4-O-[4,6-O-benzylidene-2-O-(prop-2-ynyl)-3-O-benzyl-β-D-mannopyranosyl]-(1->4)-2,3-O-isopropylidene-α-L-rhamnopyranoside

: (2R,4aR,6R,7S,8S,8aR)-8-Benzyloxy-6-((3aR,4R,6S,7S,7aR)-4-methoxy-2,2,6-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yloxy)-2-phenyl-7-prop-2-ynyloxy-hexahydro-pyrano[3,2-d][1,3]dioxine

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

methyl 2,3-O-isopropylidene-α-L-rhamnoside; In dichloromethane; at -60 ℃; for 2h;
DOI:10.1021/jo0526789

Reference yield:

: 100-39-0
benzyl bromide

: 887471-17-2
methyl 4-O-[4,6-O-benzylidene-2-O-(prop-2-ynyl)-3-O-benzyl-β-D-mannopyranosyl]-(1->4)-2,3-O-isopropylidene-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: Bu₂SnO / toluene

1.2: 91 percent / CsF / toluene; dimethylformamide

2.1: 95 percent / NaH / dimethylformamide; various solvent(s); toluene / 3 h

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

3.2: CH₂Cl₂ / 2 h / -60 °C

With 1-benzenesulfinyl piperidine; sodium hydride; di(n-butyl)tin oxide; trifluoromethanesulfonic acid anhydride; 2,4,6-tri-tert-butylpyrimidine; In dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo0526789

Reference yield:

: 158716-07-5
phenyl 3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside

: 887471-17-2
methyl 4-O-[4,6-O-benzylidene-2-O-(prop-2-ynyl)-3-O-benzyl-β-D-mannopyranosyl]-(1->4)-2,3-O-isopropylidene-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1.1: 95 percent / NaH / dimethylformamide; various solvent(s); toluene / 3 h

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

2.2: CH₂Cl₂ / 2 h / -60 °C

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