benzyl 6,7,8,9-tetradeoxy-2,3-O-isopropylidene-α-D-lyxo-8-nonen-4-ulopyranoside

Base Information

Chemical Name:benzyl 6,7,8,9-tetradeoxy-2,3-O-isopropylidene-α-D-lyxo-8-nonen-4-ulopyranoside
CAS No.:140182-79-2
Molecular Formula:C₁₉H₂₄O₅
Molecular Weight:332.397
Hs Code.:

Synonyms:benzyl 6,7,8,9-tetradeoxy-2,3-O-isopropylidene-α-D-lyxo-8-nonen-4-ulopyranoside

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Chemical Property of benzyl 6,7,8,9-tetradeoxy-2,3-O-isopropylidene-α-D-lyxo-8-nonen-4-ulopyranoside

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Technology Process of benzyl 6,7,8,9-tetradeoxy-2,3-O-isopropylidene-α-D-lyxo-8-nonen-4-ulopyranoside

There total 6 articles about benzyl 6,7,8,9-tetradeoxy-2,3-O-isopropylidene-α-D-lyxo-8-nonen-4-ulopyranoside 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:

: 15548-45-5
(2S,3S,4S,5S,6R)-2-benzyloxy-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol

: 140182-79-2
benzyl 6,7,8,9-tetradeoxy-2,3-O-isopropylidene-α-D-lyxo-8-nonen-4-ulopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1: 75 percent / pyridine / CH₂Cl₂ / 2 h / Ambient temperature

2: 94.3 percent / 2-naphthalenesulfonic acid / acetone / 8 h / Ambient temperature

3: 94 percent / triethylamine / tetrahydrofuran / Ambient temperature

4: 1.) Mg / 1.) ether, reflux, overnight, 2.) ether, reflux, 2 h

5: 98 percent / (nBu)4NF*3H₂O / tetrahydrofuran / Ambient temperature

6: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -60 deg C, 15 min. 2.) CH₂Cl₂, -60 deg C, 5 min.

With pyridine; oxalyl dichloride; naphthalene-2-sulfonate; tetrabutyl ammonium fluoride; magnesium; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; acetone;
DOI:10.1246/bcsj.65.567

Reference yield:

: 117371-06-9
benzyl 6-O-p-toluenesulfonyl-α-D-mannopyranoside

: 140182-79-2
benzyl 6,7,8,9-tetradeoxy-2,3-O-isopropylidene-α-D-lyxo-8-nonen-4-ulopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 94.3 percent / 2-naphthalenesulfonic acid / acetone / 8 h / Ambient temperature

2: 94 percent / triethylamine / tetrahydrofuran / Ambient temperature

3: 1.) Mg / 1.) ether, reflux, overnight, 2.) ether, reflux, 2 h

4: 98 percent / (nBu)4NF*3H₂O / tetrahydrofuran / Ambient temperature

5: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -60 deg C, 15 min. 2.) CH₂Cl₂, -60 deg C, 5 min.

With oxalyl dichloride; naphthalene-2-sulfonate; tetrabutyl ammonium fluoride; magnesium; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; acetone;
DOI:10.1246/bcsj.65.567

Reference yield:

: 140428-22-4
benzyl 2,3-O-isopropylidene-6,7,8,9-tetradeoxy-4-O-trimethylsilyl-α-D-manno-8-nonenopyranoside

: 140182-79-2
benzyl 6,7,8,9-tetradeoxy-2,3-O-isopropylidene-α-D-lyxo-8-nonen-4-ulopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: 98 percent / (nBu)4NF*3H₂O / tetrahydrofuran / Ambient temperature

2: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -60 deg C, 15 min. 2.) CH₂Cl₂, -60 deg C, 5 min.

With oxalyl dichloride; tetrabutyl ammonium fluoride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran;
DOI:10.1246/bcsj.65.567