phenyl-1-thio 2,3-dideoxy-3-C-[(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)methyl]-4,6-di-O-benzyl-α-D-arabino-hexopyranoside

Base Information

Chemical Name:phenyl-1-thio 2,3-dideoxy-3-C-[(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)methyl]-4,6-di-O-benzyl-α-D-arabino-hexopyranoside
CAS No.:1314380-20-5
Molecular Formula:C₆₁H₆₄O₈S
Molecular Weight:957.24
Hs Code.:

Synonyms:phenyl-1-thio 2,3-dideoxy-3-C-[(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)methyl]-4,6-di-O-benzyl-α-D-arabino-hexopyranoside

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Chemical Property of phenyl-1-thio 2,3-dideoxy-3-C-[(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)methyl]-4,6-di-O-benzyl-α-D-arabino-hexopyranoside

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Technology Process of phenyl-1-thio 2,3-dideoxy-3-C-[(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)methyl]-4,6-di-O-benzyl-α-D-arabino-hexopyranoside

There total 12 articles about phenyl-1-thio 2,3-dideoxy-3-C-[(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)methyl]-4,6-di-O-benzyl-α-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:

: 1314380-16-9
(S)-2-benzyloxy-1-phenylethyl 2,3-dideoxy-3-C-[(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)methyl]-4,6-di-O-benzyl-β-D-arabino-hexopyranoside

: 108-98-5
thiophenol

: 1314380-21-6
phenyl-1-thio 2,3-dideoxy-3-C-[(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)methyl]-4,6-di-O-benzyl-β-D-arabino-hexopyranoside

: 1314380-20-5
phenyl-1-thio 2,3-dideoxy-3-C-[(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)methyl]-4,6-di-O-benzyl-α-D-arabino-hexopyranoside

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane; at -78 - 20 ℃; for 2h; optical yield given as %de; Inert atmosphere;
DOI:10.1016/j.tet.2011.04.044

Reference yield:

: 1314380-12-5
(2R,4R)-2-[(S)-2-(benzyloxy)-1-phenylethoxy]-4-[(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)methyl]-6-formyl-3,4-dihydro-2H-pyran

: 1314380-21-6
phenyl-1-thio 2,3-dideoxy-3-C-[(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)methyl]-4,6-di-O-benzyl-β-D-arabino-hexopyranoside

: 1314380-20-5
phenyl-1-thio 2,3-dideoxy-3-C-[(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)methyl]-4,6-di-O-benzyl-α-D-arabino-hexopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: tetrahydrofuran / 16 h / 0 - 20 °C

1.2: 0.5 h / 20 °C

2.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 20 °C

2.2: 18 h / 20 - 40 °C

3.1: boron trifluoride diethyl etherate / dichloromethane / 2 h / -78 - 20 °C / Inert atmosphere

With boron trifluoride diethyl etherate; sodium hydride; In tetrahydrofuran; dichloromethane; mineral oil;
DOI:10.1016/j.tet.2011.04.044

Reference yield:

: perbenzylated D-mannopyranosylprop-2-ene

: 1314380-21-6
phenyl-1-thio 2,3-dideoxy-3-C-[(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)methyl]-4,6-di-O-benzyl-β-D-arabino-hexopyranoside

: 1314380-20-5
phenyl-1-thio 2,3-dideoxy-3-C-[(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)methyl]-4,6-di-O-benzyl-α-D-arabino-hexopyranoside

Guidance literature:: Multi-step reaction with 9 steps

1.1: ozone / methanol; dichloromethane / 0.33 h / -78 °C

1.2: 72 h / -78 - 20 °C

2.1: chloroform / 48 h / 50 °C

3.1: tris(6,6,7,7,8,8-heptafluoro-2,2-dimethyl-3,5-octadionato)europium(III) / dichloromethane / 48 h / 20 °C / Sonication

4.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere

5.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 20 °C

5.2: 18 h / 20 - 40 °C

6.1: methyl trifluoromethanesulfonate / acetonitrile / 0.25 h / 20 °C / Molecular sieve

6.2: 0.25 h / 20 °C

6.3: 0.33 h / 20 °C

7.1: tetrahydrofuran / 16 h / 0 - 20 °C

7.2: 0.5 h / 20 °C

8.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 20 °C

8.2: 18 h / 20 - 40 °C

9.1: boron trifluoride diethyl etherate / dichloromethane / 2 h / -78 - 20 °C / Inert atmosphere

With lithium aluminium tetrahydride; tris(6,6,7,7,8,8-heptafluoro-2,2-dimethyl-3,5-octadionato)europium(III); boron trifluoride diethyl etherate; sodium hydride; ozone; methyl trifluoromethanesulfonate; In tetrahydrofuran; methanol; dichloromethane; chloroform; acetonitrile; mineral oil; 2.1: Wittig reaction;
DOI:10.1016/j.tet.2011.04.044