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

Base Information

Chemical Name:methyl 2-O-benzyl-7,7-dibromo-6,7-dideoxy-3,4-O-isopropylidene-β-D-galacto-hept-6-enopyranoside
CAS No.:306300-19-6
Molecular Formula:C₁₈H₂₂Br₂O₅
Molecular Weight:478.178
Hs Code.:

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

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

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

There total 6 articles about methyl 2-O-benzyl-7,7-dibromo-6,7-dideoxy-3,4-O-isopropylidene-β-D-galacto-hept-6-enopyranoside 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: 76.0%

: 558-13-4
carbon tetrabromide

: 306768-38-7
methyl 2-O-benzyl-3,4-O-isopropylidene-β-D-galacto-hexodialdo-pyranoside

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

Guidance literature:: With triethylamine; triphenylphosphine; In dichloromethane; at 0 - 20 ℃;
DOI:10.1021/jo0005619

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 3 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

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

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 4 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

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