phenyl 4,6-O-benzylidene-2,3-dideoxy-2-C-p-tolylsulfonyl-β-D-erythro-hex-2-enopyranoside

Base Information

• Chemical Name: phenyl 4,6-O-benzylidene-2,3-dideoxy-2-C-p-tolylsulfonyl-β-D-erythro-hex-2-enopyranoside
• CAS No.: 116113-88-3
• Molecular Formula: C₂₆H₂₄O₆S
• Molecular Weight: 464.539

Synonyms:phenyl 4,6-O-benzylidene-2,3-dideoxy-2-C-p-tolylsulfonyl-β-D-erythro-hex-2-enopyranoside

Chemical Property of phenyl 4,6-O-benzylidene-2,3-dideoxy-2-C-p-tolylsulfonyl-β-D-erythro-hex-2-enopyranoside

Chemical Property:

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Technology Process of phenyl 4,6-O-benzylidene-2,3-dideoxy-2-C-p-tolylsulfonyl-β-D-erythro-hex-2-enopyranoside

There total 2 articles about phenyl 4,6-O-benzylidene-2,3-dideoxy-2-C-p-tolylsulfonyl-β-D-erythro-hex-2-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: 84.0%

phenyl 4,6-O-benzylidene-2,3-dideoxy-3-C-nitro-2-C-p-tolylsulfonyl-β-D-glucopyranoside (116113-84-9) → phenyl 4,6-O-benzylidene-2,3-dideoxy-2-C-p-tolylsulfonyl-β-D-erythro-hex-2-enopyranoside (116113-88-3)

Guidance literature:

With triethylamine; In dichloromethane; for 0.5h; Ambient temperature;

DOI:10.1016/0008-6215(87)80250-1

Reference yield:

(4aR,6S,8aS)-8-Nitro-6-phenoxy-2-phenyl-4,4a,6,8a-tetrahydro-pyrano[3,2-d][1,3]dioxine (39727-46-3) → phenyl 4,6-O-benzylidene-2,3-dideoxy-2-C-p-tolylsulfonyl-β-D-erythro-hex-2-enopyranoside (116113-88-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / tributylhexadecylphosphonium bromide / acetic acid; benzene; H₂O / 4 h / Ambient temperature

2: 84 percent / Et₃N / CH₂Cl₂ / 0.5 h / Ambient temperature

With triethylamine; cetyltributylphosphonium bromide; In dichloromethane; water; acetic acid; benzene;

DOI:10.1016/0008-6215(87)80250-1

Reference yield: 97.0%

phenyl 4,6-O-benzylidene-2,3-dideoxy-2-C-p-tolylsulfonyl-β-D-erythro-hex-2-enopyranoside (116113-88-3) → 1,5-Anhydro-4,6-O-benzylidene-2,3-dideoxy-2-C-p-tolylsulfonyl-D-erythro-hex-1-enitol (138639-22-2)

Guidance literature:

With sodium tetrahydroborate; In acetonitrile; for 15.5h; Ambient temperature;

DOI:10.1016/0008-6215(91)80017-H

upstream raw materials:

phenyl 4,6-O-benzylidene-2,3-dideoxy-3-C-nitro-2-C-p-tolylsulfonyl-β-D-glucopyranoside

(4aR,6S,8aS)-8-Nitro-6-phenoxy-2-phenyl-4,4a,6,8a-tetrahydro-pyrano[3,2-d][1,3]dioxine

Downstream raw materials:

1,5-Anhydro-4,6-O-benzylidene-2-deoxy-3-O-methyl-2-C-p-tolylsulfonyl-D-arabino-hex-1-enitol

Methyl 4,6-O-benzylidene-2-deoxy-3-O-methyl-2-C-p-tolylsulfonyl-β-D-glucopyranoside

3-O-Acetyl-1,5-anhydro-4,6-O-benzylidene-2-deoxy-2-C-p-tolylsulfonyl-D-arabino-hex-1-enitol

1,5-Anhydro-4,6-O-benzylidene-2,3-dideoxy-2-C-p-tolylsulfonyl-D-erythro-hex-1-enitol

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