methyl 2-O-benzyl-6,7-dideoxy-3,4-O-isopropylidene-β-D-galacto-hept-6-ynopyranoside

Base Information

Chemical Name:methyl 2-O-benzyl-6,7-dideoxy-3,4-O-isopropylidene-β-D-galacto-hept-6-ynopyranoside
CAS No.:306300-04-9
Molecular Formula:C₁₈H₂₂O₅
Molecular Weight:318.37
Hs Code.:

Synonyms:methyl 2-O-benzyl-6,7-dideoxy-3,4-O-isopropylidene-β-D-galacto-hept-6-ynopyranoside

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Chemical Property of methyl 2-O-benzyl-6,7-dideoxy-3,4-O-isopropylidene-β-D-galacto-hept-6-ynopyranoside

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Technology Process of methyl 2-O-benzyl-6,7-dideoxy-3,4-O-isopropylidene-β-D-galacto-hept-6-ynopyranoside

There total 7 articles about methyl 2-O-benzyl-6,7-dideoxy-3,4-O-isopropylidene-β-D-galacto-hept-6-ynopyranoside 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%

: 306300-19-6
methyl 2-O-benzyl-7,7-dibromo-6,7-dideoxy-3,4-O-isopropylidene-β-D-galacto-hept-6-enopyranoside

: 306300-04-9
methyl 2-O-benzyl-6,7-dideoxy-3,4-O-isopropylidene-β-D-galacto-hept-6-ynopyranoside

Guidance literature:: With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃;
DOI:10.1021/jo0005619

Reference yield:

: 6-O-(t-butyldimethylsilyl)-3,4-O-isopropylidene-1-O-methyl-β-D-galactopyranoside

: 306300-04-9
methyl 2-O-benzyl-6,7-dideoxy-3,4-O-isopropylidene-β-D-galacto-hept-6-ynopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 6.73 g / NaH / dimethylformamide; various solvent(s) / 3 h / 20 °C

2: 4.91 g / n-Bu₄NF / tetrahydrofuran / 2 h / 20 °C

3: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -40 - 20 °C

4: 76 percent / PPh₃; Et₃N / CH₂Cl₂ / 0 - 20 °C

5: 72 percent / LDA / tetrahydrofuran / -78 °C

With oxalyl dichloride; tetrabutyl ammonium fluoride; sodium hydride; dimethyl sulfoxide; triethylamine; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 1: Addition / 2: Elimination / 3: Oxidation / 4: dibromomethylenation / 5: Dehydrobromination;
DOI:10.1021/jo0005619

Reference yield:

: 306300-17-4
2-O-benzyl-3,4-O-isopropylidene-6-O-tert-butyldimethylsilyl-β-D-galactopyranoside

: 306300-04-9
methyl 2-O-benzyl-6,7-dideoxy-3,4-O-isopropylidene-β-D-galacto-hept-6-ynopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 4.91 g / n-Bu₄NF / tetrahydrofuran / 2 h / 20 °C

2: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -40 - 20 °C

3: 76 percent / PPh₃; Et₃N / CH₂Cl₂ / 0 - 20 °C

4: 72 percent / LDA / tetrahydrofuran / -78 °C

With oxalyl dichloride; tetrabutyl ammonium fluoride; dimethyl sulfoxide; triethylamine; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; 1: Elimination / 2: Oxidation / 3: dibromomethylenation / 4: Dehydrobromination;
DOI:10.1021/jo0005619