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

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Chemical Name:(2S,4S)-2-[(R)-2-(benzyloxy)-1-phenylethoxy]-4-[(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)methyl]-6-formyl-3,4-dihydro-2H-pyran
CAS No.:1314380-15-8
Molecular Formula:C₅₆H₅₈O₉
Molecular Weight:875.071
Hs Code.:

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

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Chemical Property of (2S,4S)-2-[(R)-2-(benzyloxy)-1-phenylethoxy]-4-[(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)methyl]-6-formyl-3,4-dihydro-2H-pyran

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Technology Process of (2S,4S)-2-[(R)-2-(benzyloxy)-1-phenylethoxy]-4-[(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)methyl]-6-formyl-3,4-dihydro-2H-pyran

There total 6 articles about (2S,4S)-2-[(R)-2-(benzyloxy)-1-phenylethoxy]-4-[(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)methyl]-6-formyl-3,4-dihydro-2H-pyran 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: 75.0%

: 1314380-11-4
(2S,4S)-2-[(R)-2-(benzyloxy)-1-phenylethoxy]-4-[(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)methyl]-6-(thiazol-2-yl)-3,4-dihydro-2H-pyran

: 1314380-15-8
(2S,4S)-2-[(R)-2-(benzyloxy)-1-phenylethoxy]-4-[(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)methyl]-6-formyl-3,4-dihydro-2H-pyran

Guidance literature:: (2S,4S)-2-[(R)-2-(benzyloxy)-1-phenylethoxy]-4-[(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)methyl]-6-(thiazol-2-yl)-3,4-dihydro-2H-pyran; With methyl trifluoromethanesulfonate; In acetonitrile; at 20 ℃; for 0.25h; Molecular sieve;

With sodium tetrahydroborate; In methanol; at 20 ℃; for 0.25h;

With silver nitrate; In water; acetonitrile; at 20 ℃; for 0.333333h;
DOI:10.1016/j.tet.2011.04.044

Reference yield:

: (2,3,4,6-tetra-O-benzyl-D-mannopyranosyl)-ethanal

: 1314380-15-8
(2S,4S)-2-[(R)-2-(benzyloxy)-1-phenylethoxy]-4-[(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)methyl]-6-formyl-3,4-dihydro-2H-pyran

Guidance literature:: Multi-step reaction with 5 steps

1.1: chloroform / 30 h / 50 °C

2.1: tris(6,6,7,7,8,8-heptafluoro-2,2-dimethyl-3,5-octadionato)europium(III) / dichloromethane / 24 h / 20 °C / Sonication

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

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

4.2: 18 h / 20 - 40 °C

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

5.2: 0.25 h / 20 °C

5.3: 0.33 h / 20 °C

With lithium aluminium tetrahydride; tris(6,6,7,7,8,8-heptafluoro-2,2-dimethyl-3,5-octadionato)europium(III); sodium hydride; methyl trifluoromethanesulfonate; In tetrahydrofuran; dichloromethane; chloroform; acetonitrile; mineral oil; 1.1: Wittig reaction;
DOI:10.1016/j.tet.2011.04.044

Reference yield:

: C₅₁H₅₃NO₈S

: 1314380-15-8
(2S,4S)-2-[(R)-2-(benzyloxy)-1-phenylethoxy]-4-[(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)methyl]-6-formyl-3,4-dihydro-2H-pyran

Guidance literature:: Multi-step reaction with 2 steps

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

1.2: 18 h / 20 - 40 °C

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

2.2: 0.25 h / 20 °C

2.3: 0.33 h / 20 °C

With sodium hydride; methyl trifluoromethanesulfonate; In tetrahydrofuran; acetonitrile; mineral oil;
DOI:10.1016/j.tet.2011.04.044