1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-2-C-(phenylthiomethyl)-D-lyxo-hex-1-enitol

Base Information

• Chemical Name: 1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-2-C-(phenylthiomethyl)-D-lyxo-hex-1-enitol
• CAS No.: 1350934-06-3
• Molecular Formula: C₃₄H₃₄O₄S
• Molecular Weight: 538.708

Synonyms:1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-2-C-(phenylthiomethyl)-D-lyxo-hex-1-enitol

Chemical Property of 1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-2-C-(phenylthiomethyl)-D-lyxo-hex-1-enitol

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Technology Process of 1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-2-C-(phenylthiomethyl)-D-lyxo-hex-1-enitol

There total 4 articles about 1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-2-C-(phenylthiomethyl)-D-lyxo-hex-1-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: 87.0%

thiophenol (108-98-5) + 3,4,6-tri-O-benzyl-2-C-acetoxymethylgalactal (153081-97-1) → 1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-2-C-(phenylthiomethyl)-D-lyxo-hex-1-enitol (1350934-06-3) + C34H34O4S

Guidance literature:

With indium(III) chloride; In acetonitrile; at 0 ℃; for 0.25h; regioselective reaction; Inert atmosphere;

DOI:10.1016/j.tet.2011.09.122

Reference yield: 70.0%

1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-2-C-benzyloxymethyl-D-lyxo-hex-1-enitol (1092103-65-5) + thiophenol (108-98-5) → 1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-2-C-(phenylthiomethyl)-D-lyxo-hex-1-enitol (1350934-06-3) + C34H34O4S

Guidance literature:

With indium(III) chloride; In acetonitrile; at 0 ℃; for 0.25h; regioselective reaction; Inert atmosphere;

DOI:10.1016/j.tet.2011.09.122

Reference yield: 66.0%

thiophenol (108-98-5) + 1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-2-hydroxymethyl-D-lyxo-hex-1-enitol (153496-00-5) → 1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-2-C-(phenylthiomethyl)-D-lyxo-hex-1-enitol (1350934-06-3)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In benzene; at 0 ℃; for 0.5h; regioselective reaction;

DOI:10.1016/j.tet.2011.09.122

upstream raw materials:

1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-2-C-methoxymethyl-D-lyxo-hex-1-enitol

thiophenol

1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-2-C-benzyloxymethyl-D-lyxo-hex-1-enitol

1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-2-hydroxymethyl-D-lyxo-hex-1-enitol

Downstream raw materials:

benzyl 4,6-di-O-benzyl-2,3-dideoxy-2-C-(phenylthiomethyl)-D-threo-hex-2-enopyranoside

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