methyl 4-O-benzyl-2,3,6,7-tetradeoxy-2,6-di-O-C-methyl-α-D-arabino-hept-6-enopyranoside

Base Information

Chemical Name:methyl 4-O-benzyl-2,3,6,7-tetradeoxy-2,6-di-O-C-methyl-α-D-arabino-hept-6-enopyranoside
CAS No.:137964-43-3
Molecular Formula:C₁₇H₂₄O₃
Molecular Weight:276.376
Hs Code.:

Synonyms:methyl 4-O-benzyl-2,3,6,7-tetradeoxy-2,6-di-O-C-methyl-α-D-arabino-hept-6-enopyranoside

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Chemical Property of methyl 4-O-benzyl-2,3,6,7-tetradeoxy-2,6-di-O-C-methyl-α-D-arabino-hept-6-enopyranoside

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Technology Process of methyl 4-O-benzyl-2,3,6,7-tetradeoxy-2,6-di-O-C-methyl-α-D-arabino-hept-6-enopyranoside

There total 10 articles about methyl 4-O-benzyl-2,3,6,7-tetradeoxy-2,6-di-O-C-methyl-α-D-arabino-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:

: 1-((2R,3S,5S)-3-Benzyloxy-6-methoxy-5-methyl-tetrahydro-pyran-2-yl)-ethanol

: 137964-43-3
methyl 4-O-benzyl-2,3,6,7-tetradeoxy-2,6-di-O-C-methyl-α-D-arabino-hept-6-enopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: 79 percent / MS 3AP, PCC / CH₂Cl₂ / 3 h / Ambient temperature

2: 1.) butyllithium / 1.) ether, hexane, 0 deg C, 15 min, 2.) ether, hexane, RT, 20 h

With n-butyllithium; pyridinium chlorochromate; In dichloromethane;
DOI:10.1246/bcsj.65.2974

Reference yield:

: (2S,3S,5S)-3-Benzyloxy-6-methoxy-5-methyl-tetrahydro-pyran-2-carbaldehyde

: 137964-43-3
methyl 4-O-benzyl-2,3,6,7-tetradeoxy-2,6-di-O-C-methyl-α-D-arabino-hept-6-enopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: CH₂Cl₂; diethyl ether; tetrahydrofuran / 1 h / -78 °C

2: 79 percent / MS 3AP, PCC / CH₂Cl₂ / 3 h / Ambient temperature

3: 1.) butyllithium / 1.) ether, hexane, 0 deg C, 15 min, 2.) ether, hexane, RT, 20 h

With n-butyllithium; pyridinium chlorochromate; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1246/bcsj.65.2974

Reference yield:

: methyl 4-O-benzyl-2,3-dideoxy-2-C-methyl-D-arabinohexopyranoside

: 137964-43-3
methyl 4-O-benzyl-2,3,6,7-tetradeoxy-2,6-di-O-C-methyl-α-D-arabino-hept-6-enopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: oxalyl chloride, DMSO / CH₂Cl₂ / 45 h / -78 °C

2: CH₂Cl₂; diethyl ether; tetrahydrofuran / 1 h / -78 °C

3: 79 percent / MS 3AP, PCC / CH₂Cl₂ / 3 h / Ambient temperature

4: 1.) butyllithium / 1.) ether, hexane, 0 deg C, 15 min, 2.) ether, hexane, RT, 20 h

With n-butyllithium; oxalyl dichloride; dimethyl sulfoxide; pyridinium chlorochromate; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1246/bcsj.65.2974