2,6-Anhydro-5-deoxy-1,3-O-isopropylidene-phenylsulfonyl-D-arabino-hex-5-enitol

Base Information

• Chemical Name: 2,6-Anhydro-5-deoxy-1,3-O-isopropylidene-phenylsulfonyl-D-arabino-hex-5-enitol
• CAS No.: 108681-45-4
• Molecular Formula: C₁₅H₁₈O₆S
• Molecular Weight: 326.37

Synonyms:2,6-Anhydro-5-deoxy-1,3-O-isopropylidene-phenylsulfonyl-D-arabino-hex-5-enitol

Chemical Property of 2,6-Anhydro-5-deoxy-1,3-O-isopropylidene-phenylsulfonyl-D-arabino-hex-5-enitol

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Technology Process of 2,6-Anhydro-5-deoxy-1,3-O-isopropylidene-phenylsulfonyl-D-arabino-hex-5-enitol

There total 7 articles about 2,6-Anhydro-5-deoxy-1,3-O-isopropylidene-phenylsulfonyl-D-arabino-hex-5-enitol 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: 96.0%

2,3:4,6-Di-O-isopropylidene-β-D-galactopyranosyl phenyl sulfone → 2,6-Anhydro-5-deoxy-1,3-O-isopropylidene-phenylsulfonyl-D-arabino-hex-5-enitol (108681-45-4)

Guidance literature:

With methyllithium lithium bromide; In tetrahydrofuran; at -78 ℃; for 0.333333h;

DOI:10.1055/s-2001-10802

Reference yield:

(3aS,4R,5aR,9aR,9bS)-4-Benzenesulfonyl-2,2,8,8-tetramethyl-hexahydro-[1,3]dioxolo[4',5':4,5]pyrano[3,2-d][1,3]dioxine (108681-44-3) → 2,6-Anhydro-5-deoxy-1,3-O-isopropylidene-phenylsulfonyl-D-arabino-hex-5-enitol (108681-45-4) + acetone (67-64-1)

Guidance literature:

With methyllithium; In tetrahydrofuran; for 0.5h; Yield given; Heating;

DOI:10.1016/S0040-4039(00)94273-4

Reference yield:

1-phenylthio-1-deoxy-2,3,4,6-di-(O-isopropylidene)-β-D-glucopyranoside (345197-64-0) → 2,6-Anhydro-5-deoxy-1,3-O-isopropylidene-phenylsulfonyl-D-arabino-hex-5-enitol (108681-45-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / MCPBA; NaHCO₃ / CH₂Cl₂ / 12 h / 0 - 20 °C

2: 96 percent / MeLi*LiBr / tetrahydrofuran / 0.33 h / -78 °C

With methyllithium lithium bromide; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1055/s-2001-10802

upstream raw materials:

(3aS,4R,5aR,9aR,9bS)-4-Benzenesulfonyl-2,2,8,8-tetramethyl-hexahydro-[1,3]dioxolo[4',5':4,5]pyrano[3,2-d][1,3]dioxine

1-phenylthio-1-deoxy-2,3,4,6-di-(O-isopropylidene)-β-D-glucopyranoside

phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside

(2R,3S,4S,5S,6R)-2-Benzenesulfonyl-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

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