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

Base Information

• Chemical Name: (2R,4R)-2-[(S)-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.: 1314380-14-7
• Molecular Formula: C₅₆H₅₈O₉
• Molecular Weight: 875.071

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

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

Chemical Property:

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Technology Process of (2R,4R)-2-[(S)-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 (2R,4R)-2-[(S)-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: 73.0%

(2R,4R)-2-[(S)-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 (1314380-10-3) → (2R,4R)-2-[(S)-2-(benzyloxy)-1-phenylethoxy]-4-[(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)methyl]-6-formyl-3,4-dihydro-2H-pyran (1314380-14-7)

Guidance literature:

(2R,4R)-2-[(S)-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 → (2R,4R)-2-[(S)-2-(benzyloxy)-1-phenylethoxy]-4-[(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)methyl]-6-formyl-3,4-dihydro-2H-pyran (1314380-14-7)

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:

(E)-4-(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)-1-(thiazol-2-yl)-but-2-en-1-one (1314380-02-3) → (2R,4R)-2-[(S)-2-(benzyloxy)-1-phenylethoxy]-4-[(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)methyl]-6-formyl-3,4-dihydro-2H-pyran (1314380-14-7)

Guidance literature:

Multi-step reaction with 4 steps

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

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

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

3.2: 18 h / 20 - 40 °C

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

4.2: 0.25 h / 20 °C

4.3: 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; acetonitrile; mineral oil;

DOI:10.1016/j.tet.2011.04.044

upstream raw materials:

(2R,4R)-2-[(S)-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

(E)-4-(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)-1-(thiazol-2-yl)-but-2-en-1-one

methyl (S)-2-phenyl-2-{[(2R,4R)-4-(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)methyl-6-(thiazol-2-yl)-3,4-dihydro-2H-pyran-2-yl]oxy}acetate

methyl (S)-(ethenyloxy)(phenyl)acetate

Downstream raw materials:

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

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

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

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