phenyl 2-deoxy-3,4,6-tris-O-(phenylmethyl)-1-thio-D-arabino-hexopyranoside

Base Information

• Chemical Name: phenyl 2-deoxy-3,4,6-tris-O-(phenylmethyl)-1-thio-D-arabino-hexopyranoside
• CAS No.: 119070-22-3
• Molecular Formula: C₃₃H₃₄O₄S
• Molecular Weight: 526.697

Synonyms:phenyl 2-deoxy-3,4,6-tris-O-(phenylmethyl)-1-thio-D-arabino-hexopyranoside

Chemical Property of phenyl 2-deoxy-3,4,6-tris-O-(phenylmethyl)-1-thio-D-arabino-hexopyranoside

Chemical Property:

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Technology Process of phenyl 2-deoxy-3,4,6-tris-O-(phenylmethyl)-1-thio-D-arabino-hexopyranoside

There total 16 articles about phenyl 2-deoxy-3,4,6-tris-O-(phenylmethyl)-1-thio-D-arabino-hexopyranoside 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: 82.0%

thiophenol (108-98-5) + (4R)-4-[[2-deoxy-3,4,6-tris-O-(phenylmethyl)-α-D-arabino-hexopyranosyl]oxy]-2-pentanone (182314-16-5) → (-)-(4R)-4-hydroxypentan-2-one (63315-69-5) + phenyl 2-deoxy-3,4,6-tris-O-(phenylmethyl)-1-thio-D-arabino-hexopyranoside (119070-22-3) + (S)-4-hydroxypentan-2-one (73836-68-7)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; -78 deg C -> room temperature;

DOI:10.1021/jo961499b

Reference yield: 82.0%

thiophenol (108-98-5) + (4R)-4-[[2-deoxy-3,4,6-tris-O-(phenylmethyl)-α-D-arabino-hexopyranosyl]oxy]-2-octanone (182314-18-7) → phenyl 2-deoxy-3,4,6-tris-O-(phenylmethyl)-1-thio-D-arabino-hexopyranoside (119070-22-3) + (4R)-4-hydroxy-2-octanone (65651-62-9) + (4S)-4-hydroxy-2-octanone

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; -78 deg C -> room temperature;

DOI:10.1021/jo961499b

Reference yield: 40.0%

C34H36O7S + thiophenol (108-98-5) → phenyl 2-deoxy-3,4,6-tris-O-(phenylmethyl)-1-thio-D-arabino-hexopyranoside (119070-22-3)

Guidance literature:

In tetrahydrofuran; at -78 - 20 ℃;

upstream raw materials:

chloro-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranoside

thiophenol

(4R)-4-[[2-deoxy-3,4,6-tris-O-(phenylmethyl)-α-D-arabino-hexopyranosyl]oxy]-2-pentanone

(4R)-4-[[2-deoxy-3,4,6-tris-O-(phenylmethyl)-α-D-arabino-hexopyranosyl]oxy]-2-octanone

Downstream raw materials:

phenyl 3,4,6-tri-O-benzyl-2-deoxy-1-sulphonyl-αβ-D-arabino-pyranoside

phenyl 3,4,6-tri-O-benzyl-2-deoxy-1-sulphonyl-β-D-arabino-pyranoside

phenyl 3,4,6-tri-O-benzyl-2-deoxy-1-sulphonyl-α-D-arabino-pyranoside

(2R,3S,4R)-6-Benzenesulfinyl-3,4-bis-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran

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