methyl 2,3-di-O-benzyl-6,7-dideoxy-4-O-propargyl-α-D-gluco-hept-6-enopyranoside

Base Information

Chemical Name:methyl 2,3-di-O-benzyl-6,7-dideoxy-4-O-propargyl-α-D-gluco-hept-6-enopyranoside
CAS No.:236424-97-8
Molecular Formula:C₂₅H₂₈O₅
Molecular Weight:408.494
Hs Code.:

Synonyms:methyl 2,3-di-O-benzyl-6,7-dideoxy-4-O-propargyl-α-D-gluco-hept-6-enopyranoside

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Chemical Property of methyl 2,3-di-O-benzyl-6,7-dideoxy-4-O-propargyl-α-D-gluco-hept-6-enopyranoside

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Technology Process of methyl 2,3-di-O-benzyl-6,7-dideoxy-4-O-propargyl-α-D-gluco-hept-6-enopyranoside

There total 4 articles about methyl 2,3-di-O-benzyl-6,7-dideoxy-4-O-propargyl-α-D-gluco-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: 90.0%

: 106-96-7
propargyl bromide

: 236424-93-4
methyl 2,3-di-O-benzyl-6,7-dideoxy-α-D-gluco-hept-6-enopyranoside

: 236424-97-8
methyl 2,3-di-O-benzyl-6,7-dideoxy-4-O-propargyl-α-D-gluco-hept-6-enopyranoside

Guidance literature:: With sodium hydride; mineral oil; In N,N-dimethyl-formamide; at 25 ℃; for 3h;
DOI:10.1016/S0040-4020(99)00296-3

Reference yield:

: 130523-98-7
(2S,3S,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-carbaldehyde

: 236424-97-8
methyl 2,3-di-O-benzyl-6,7-dideoxy-4-O-propargyl-α-D-gluco-hept-6-enopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: 2.07 g / n-BuLi / tetrahydrofuran / 4 h / 0 - 25 °C

2: 85 percent / DDQ; H₂O / CH₂Cl₂ / 6 h / 25 °C

3: 90 percent / NaH/mineral oil / dimethylformamide / 3 h / 25 °C

With n-butyllithium; water; sodium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; mineral oil; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 1: Wittig reaction / 2: Hydrolysis / 3: Alkylation;
DOI:10.1016/S0040-4020(99)00296-3

Reference yield:

: 90633-95-7,94827-31-3,90633-90-2
methyl 2,3-bis-O-benzyl-4-O-[(4-methoxyphenyl)methyl]-α-D-glucopyranoside

: 236424-97-8
methyl 2,3-di-O-benzyl-6,7-dideoxy-4-O-propargyl-α-D-gluco-hept-6-enopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -65 - 25 °C

2: 2.07 g / n-BuLi / tetrahydrofuran / 4 h / 0 - 25 °C

3: 85 percent / DDQ; H₂O / CH₂Cl₂ / 6 h / 25 °C

4: 90 percent / NaH/mineral oil / dimethylformamide / 3 h / 25 °C

With n-butyllithium; oxalyl dichloride; water; sodium hydride; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; mineral oil; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 1: Swern oxidation / 2: Wittig reaction / 3: Hydrolysis / 4: Alkylation;
DOI:10.1016/S0040-4020(99)00296-3