methyl 4,6-O-benzylidene-2-deoxy-2-C-propynyl-α-D-ribo-hexopyranosid-3-ulose

Base Information

Chemical Name:methyl 4,6-O-benzylidene-2-deoxy-2-C-propynyl-α-D-ribo-hexopyranosid-3-ulose
CAS No.:122674-58-2
Molecular Formula:C₁₇H₁₈O₅
Molecular Weight:302.327
Hs Code.:

Synonyms:methyl 4,6-O-benzylidene-2-deoxy-2-C-propynyl-α-D-ribo-hexopyranosid-3-ulose

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Chemical Property of methyl 4,6-O-benzylidene-2-deoxy-2-C-propynyl-α-D-ribo-hexopyranosid-3-ulose

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Technology Process of methyl 4,6-O-benzylidene-2-deoxy-2-C-propynyl-α-D-ribo-hexopyranosid-3-ulose

There total 2 articles about methyl 4,6-O-benzylidene-2-deoxy-2-C-propynyl-α-D-ribo-hexopyranosid-3-ulose 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: 50.0%

: 63598-31-2
methyl 4,6-O-(R)-benzylidene-2-deoxy-α-D-erythrohexopyranosid-3-ulose

: 106-96-7
propargyl bromide

: 122674-58-2
methyl 4,6-O-benzylidene-2-deoxy-2-C-propynyl-α-D-ribo-hexopyranosid-3-ulose

Guidance literature:: With potassium hydride; In tetrahydrofuran; at 0 ℃;
DOI:10.1021/jo00297a012

Reference yield:

: 106-96-7
propargyl bromide

: 194149-26-3
methyl 2,3:4,6-di-O-benzylidene-α-D-mannopyranoside

: 122674-58-2
methyl 4,6-O-benzylidene-2-deoxy-2-C-propynyl-α-D-ribo-hexopyranosid-3-ulose

Guidance literature:: With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; Yield given. Multistep reaction; 1.) THF, from -40 deg C to -30 deg C, 30 min, 2.) THF, from -35 deg C to -30 deg C;
DOI:10.1021/jo00283a034

Reference yield:

: 122674-58-2
methyl 4,6-O-benzylidene-2-deoxy-2-C-propynyl-α-D-ribo-hexopyranosid-3-ulose

: methyl 4,6-O-benzylidene-2,3-dideoxy-3-C-((E)-2-hydroxypropylidene)-2-C-propynyl-α-D-ribo-hexopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) NaH / 1.) THF, 0 deg C, 0.5 h, 2.) THF, RT

2: DIBAL / toluene

3: 90 percent / PCC, Celite, sodium acetate, Florisil / CH₂Cl₂ / Ambient temperature

4: 93 percent / tetrahydrofuran; toluene

With florisil; Celite; sodium acetate; sodium hydride; diisobutylaluminium hydride; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1021/jo00283a034