3'',4''-di-O-acetyl-α-L-xylopyranose 1'',2''--2'-yl orthoacetate

Base Information

• Chemical Name: 3'',4''-di-O-acetyl-α-L-xylopyranose 1'',2''--2'-yl orthoacetate
• CAS No.: 224622-57-5
• Molecular Formula: C₆₁H₆₀O₂₂
• Molecular Weight: 1145.13

Synonyms:3'',4''-di-O-acetyl-α-L-xylopyranose 1'',2''--2'-yl orthoacetate

Chemical Property of 3'',4''-di-O-acetyl-α-L-xylopyranose 1'',2''--2'-yl orthoacetate

Chemical Property:

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Technology Process of 3'',4''-di-O-acetyl-α-L-xylopyranose 1'',2''--2'-yl orthoacetate

There total 10 articles about 3'',4''-di-O-acetyl-α-L-xylopyranose 1'',2''--2'-yl orthoacetate 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: 94.0%

allyl 4-O-(3,4-di-O-benzoyl-α-L-rhamnopyranosyl)-2,3,6-tri-O-benzoyl-α-D-mannopyranoside (224622-54-2) + 2,3,4-tri-O-acetyl-α-L-xylopyranosyl bromide (65914-26-3) → 3'',4''-di-O-acetyl-α-L-xylopyranose 1'',2''--2'-yl orthoacetate (224622-57-5)

Guidance literature:

With 2,4-lutidine; 4 A molecular sieve; silver trifluoromethanesulfonate; In dichloromethane; Ambient temperature;

DOI:10.1080/07328309908543994

Reference yield:

benzoyl chloride (98-88-4) → 3'',4''-di-O-acetyl-α-L-xylopyranose 1'',2''--2'-yl orthoacetate (224622-57-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 76 percent / pyridine / 0 - 20 °C

2: 1.) molecular sieves 4 Angstroem, 2.) trimethylsilyl triflate / 1.) CH₂Cl₂, room temperature, 1 h, 2.) CH₂Cl₂, 40 min

3: 96 percent / AcCl / methanol / 48 - 54 °C

4: 94 percent / 2,4-lutidine, molecular sieves 4 Angstroem, silver triflate / CH₂Cl₂ / Ambient temperature

With pyridine; 2,4-lutidine; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; silver trifluoromethanesulfonate; acetyl chloride; In methanol; dichloromethane;

DOI:10.1080/07328309908543994

Reference yield:

allyl α-D-mannopyranoside (41308-76-3,821794-45-0) → 3'',4''-di-O-acetyl-α-L-xylopyranose 1'',2''--2'-yl orthoacetate (224622-57-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 76 percent / pyridine / 0 - 20 °C

2: 1.) molecular sieves 4 Angstroem, 2.) trimethylsilyl triflate / 1.) CH₂Cl₂, room temperature, 1 h, 2.) CH₂Cl₂, 40 min

3: 96 percent / AcCl / methanol / 48 - 54 °C

4: 94 percent / 2,4-lutidine, molecular sieves 4 Angstroem, silver triflate / CH₂Cl₂ / Ambient temperature

With pyridine; 2,4-lutidine; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; silver trifluoromethanesulfonate; acetyl chloride; In methanol; dichloromethane;

DOI:10.1080/07328309908543994

upstream raw materials:

allyl 4-O-(3,4-di-O-benzoyl-α-L-rhamnopyranosyl)-2,3,6-tri-O-benzoyl-α-D-mannopyranoside

2,3,4-tri-O-acetyl-α-L-xylopyranosyl bromide

allyl α-D-mannopyranoside

benzoyl chloride

Downstream raw materials:

allyl 4-O-<2-O-(2,3,4-tri-O-acetyl-β-L-xylopyranosyl)-3,4-di-O-benzoyl-α-L-rhamnopyranosyl>-2,3,6-tri-O-benzoyl-α-D-mannopyranoside

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