phenyl 2,3-di-O-acetyl-4,6-O-(2'-naphthyl)methylene-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: phenyl 2,3-di-O-acetyl-4,6-O-(2'-naphthyl)methylene-1-thio-β-D-glucopyranoside
• CAS No.: 1393472-03-1
• Molecular Formula: C₂₇H₂₆O₇S
• Molecular Weight: 494.565

Synonyms:phenyl 2,3-di-O-acetyl-4,6-O-(2'-naphthyl)methylene-1-thio-β-D-glucopyranoside

Chemical Property of phenyl 2,3-di-O-acetyl-4,6-O-(2'-naphthyl)methylene-1-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

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Technology Process of phenyl 2,3-di-O-acetyl-4,6-O-(2'-naphthyl)methylene-1-thio-β-D-glucopyranoside

There total 2 articles about phenyl 2,3-di-O-acetyl-4,6-O-(2'-naphthyl)methylene-1-thio-β-D-glucopyranoside 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:

2-(dimethoxymethyl)naphthalene (77196-31-7) → phenyl 2,3-di-O-acetyl-4,6-O-(2'-naphthyl)methylene-1-thio-β-D-glucopyranoside (1393472-03-1)

Guidance literature:

Multi-step reaction with 2 steps

1: toluene-4-sulfonic acid / acetonitrile / 0.5 h / 60 °C

2: pyridine / 2 h / 20 °C

With pyridine; toluene-4-sulfonic acid; In acetonitrile;

DOI:10.1016/j.tet.2012.06.081

Reference yield:

(2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol (2936-70-1,5624-48-6,13992-15-9,16758-34-2,28244-97-5,77481-62-0,77481-63-1,105088-17-3,149495-84-1) → phenyl 2,3-di-O-acetyl-4,6-O-(2'-naphthyl)methylene-1-thio-β-D-glucopyranoside (1393472-03-1)

Guidance literature:

Multi-step reaction with 2 steps

1: toluene-4-sulfonic acid / acetonitrile / 0.5 h / 60 °C

2: pyridine / 2 h / 20 °C

With pyridine; toluene-4-sulfonic acid; In acetonitrile;

DOI:10.1016/j.tet.2012.06.081

Reference yield: 82.0%

phenyl 2,3-di-O-acetyl-4,6-O-(2'-naphthyl)methylene-1-thio-β-D-glucopyranoside (1393472-03-1) → phenyl 2,3-di-O-acetyl-6-O-(2'-naphthyl)methyl-1-thio-β-D-glucopyranoside (1393472-04-2)

Guidance literature:

With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; at 20 ℃; for 4h;

DOI:10.1016/j.tet.2012.06.081

upstream raw materials:

(2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol

2-(dimethoxymethyl)naphthalene

Downstream raw materials:

phenyl 2,3-di-O-acetyl-6-O-(2'-naphthyl)methyl-1-thio-β-D-glucopyranoside

phenyl (6-O-benzyl-2,3,4-tri-O-methyl-α-D-glucopyranosyl)-(1->4)-2,3-di-O-acetyl-6-O-(2'-naphthyl)methyl-1-thio-β-D-glucopyranoside

methyl (6-O-benzyl-2,3,4-tri-O-methyl-α-D-glucopyranosyl)-(1->4)-[2,3-di-O-acetyl-6-O-(2'-naphthyl)methyl-β-D-glucopyranosyl]-(1->4)-2,6-di-O-benzyl-3-deoxy-3-C-(methyl sulfonatomethyl)-α-D-glucopyranoside

methyl (6-O-benzyl-2,3,4-tri-O-methyl-α-D-glucopyranosyl)-(1->4)-(2,3-di-O-acetyl-β-D-glucopyranosyl)-(1->4)-2,6-di-O-benzyl-3-deoxy-3-C-(methylsulfonatomethyl)-α-D-glucopyranoside

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