Acetic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(3-hydroxy-propyl)-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(3-hydroxy-propyl)-tetrahydro-pyran-3-yl ester
• CAS No.: 440362-96-9
• Molecular Formula: C₃₂H₃₈O₇
• Molecular Weight: 534.65

Synonyms:Acetic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(3-hydroxy-propyl)-tetrahydro-pyran-3-yl ester

Chemical Property of Acetic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(3-hydroxy-propyl)-tetrahydro-pyran-3-yl ester

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Technology Process of Acetic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(3-hydroxy-propyl)-tetrahydro-pyran-3-yl ester

There total 13 articles about Acetic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(3-hydroxy-propyl)-tetrahydro-pyran-3-yl ester 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%

3-C-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glycopyranosyl)propene (193546-84-8) → Acetic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(3-hydroxy-propyl)-tetrahydro-pyran-3-yl ester (440362-96-9)

Guidance literature:

3-C-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glycopyranosyl)propene; With borane; In tetrahydrofuran; at 0 ℃; for 2h;

With sodium hydroxide; dihydrogen peroxide; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1016/S0040-4020(02)00057-1

Reference yield: 43.0%

3-C-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-glucopyranosyl)1-propoxyphthalimide → (4S)-1,4-anhydro-6,7,9-tri-O-benzyl-2,3,5-trideoxy-D-arabino-non-4-ulopyranose + 3-C-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-glucopyranosyl)-1-propanol + Acetic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(3-hydroxy-propyl)-tetrahydro-pyran-3-yl ester (440362-96-9)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; for 2h; Reflux;

DOI:10.1021/acs.joc.1c01376

Reference yield: 23.0%

3-C-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)1-propoxyphthalimide → (4S)-1,4-anhydro-6,7,9-tri-O-benzyl-2,3,5-trideoxy-D-arabino-non-4-ulopyranose + Acetic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(3-hydroxy-propyl)-tetrahydro-pyran-3-yl ester (440362-96-9)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; for 2h; Reflux;

DOI:10.1021/acs.joc.1c01376

upstream raw materials:

3-C-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glycopyranosyl)propene

3-(3,4,6-tri-O-benzyl-α-D-glucopyranosyl)-1-propene

3-(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-1-propene

3-C-(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)1-propanol

Downstream raw materials:

Acetic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(3-triisopropylsilanyloxy-propyl)-tetrahydro-pyran-3-yl ester

Acetic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(3-oxo-propyl)-tetrahydro-pyran-3-yl ester

(2S,3S,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(3-butenyl)-tetrahydro-pyran-3-acetate

(2R,3R,4S,5S,6S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-but-3-enyl-5-isopropenyloxy-tetrahydro-pyran

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