Acetic acid (2S,3R,4R,5S,6R)-6-allyloxy-4,5-bis-benzyloxy-2-methyl-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2S,3R,4R,5S,6R)-6-allyloxy-4,5-bis-benzyloxy-2-methyl-tetrahydro-pyran-3-yl ester
• CAS No.: 228394-55-6
• Molecular Formula: C₂₅H₃₀O₆
• Molecular Weight: 426.51

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

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

Chemical Property:

Purity/Quality:

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

There total 3 articles about Acetic acid (2S,3R,4R,5S,6R)-6-allyloxy-4,5-bis-benzyloxy-2-methyl-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:

benzyl bromide (100-39-0) → Acetic acid (2S,3R,4R,5S,6R)-6-allyloxy-4,5-bis-benzyloxy-2-methyl-tetrahydro-pyran-3-yl ester (228394-55-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) B₂SnO / 1.) toluene, reflux, 16 h, 2.) DMF, 90 deg C, 9 h

2: pyridine / 16 h / Ambient temperature

With pyridine; B₂SnO;

DOI:10.1021/ja990274q

Reference yield:

allyl α-L-fucopyranoside (41308-77-4) → Acetic acid (2S,3R,4R,5S,6R)-6-allyloxy-4,5-bis-benzyloxy-2-methyl-tetrahydro-pyran-3-yl ester (228394-55-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) B₂SnO / 1.) toluene, reflux, 16 h, 2.) DMF, 90 deg C, 9 h

2: pyridine / 16 h / Ambient temperature

With pyridine; B₂SnO;

DOI:10.1021/ja990274q

Reference yield:

acetic anhydride (108-24-7) + allyl 2,3-di-O-benzyl-α-L-fucopyranoside (228394-54-5) → Acetic acid (2S,3R,4R,5S,6R)-6-allyloxy-4,5-bis-benzyloxy-2-methyl-tetrahydro-pyran-3-yl ester (228394-55-6)

Guidance literature:

With pyridine; for 16h; Ambient temperature;

DOI:10.1021/ja990274q

upstream raw materials:

acetic anhydride

allyl 2,3-di-O-benzyl-α-L-fucopyranoside

benzyl bromide

allyl α-L-fucopyranoside

Downstream raw materials:

Acetic acid (2S,3R,4R,5S,6R)-4,5-bis-benzyloxy-6-[(2R,3R,4R,5R)-5-(2-benzyloxycarbonylamino-6-oxo-1,6-dihydro-purin-9-yl)-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-ylmethoxy]-2-methyl-tetrahydro-pyran-3-yl ester

Acetic acid (2S,3R,4R,5S,6S)-4,5-bis-benzyloxy-6-[(2R,3R,4R,5R)-5-(2-benzyloxycarbonylamino-6-oxo-1,6-dihydro-purin-9-yl)-4-sulfooxy-2-sulfooxymethyl-tetrahydro-furan-3-yloxy]-2-methyl-tetrahydro-pyran-3-yl ester

Acetic acid (2S,3R,4R,5S,6S)-4,5-bis-benzyloxy-6-[(2R,3S,4R,5R)-5-(2-benzyloxycarbonylamino-6-oxo-1,6-dihydro-purin-9-yl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-tetrahydro-furan-3-yloxy]-2-methyl-tetrahydro-pyran-3-yl ester

Acetic acid (2S,3R,4R,5S,6S)-4,5-bis-benzyloxy-6-[(2R,3R,4R,5R)-2-(2-benzyloxycarbonylamino-6-oxo-1,6-dihydro-purin-9-yl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-tetrahydro-furan-3-yloxy]-2-methyl-tetrahydro-pyran-3-yl ester

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