Acetic acid (2R,3R,4S,5R,6S)-4,5-diacetoxy-6-acetoxymethyl-2-phenoxy-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3R,4S,5R,6S)-4,5-diacetoxy-6-acetoxymethyl-2-phenoxy-tetrahydro-pyran-3-yl ester
• CAS No.: 39031-67-9
• Molecular Formula: C₂₀H₂₄O₁₀
• Molecular Weight: 424.405

Synonyms:Acetic acid (2R,3R,4S,5R,6S)-4,5-diacetoxy-6-acetoxymethyl-2-phenoxy-tetrahydro-pyran-3-yl ester

Chemical Property of Acetic acid (2R,3R,4S,5R,6S)-4,5-diacetoxy-6-acetoxymethyl-2-phenoxy-tetrahydro-pyran-3-yl ester

Chemical Property:

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Technology Process of Acetic acid (2R,3R,4S,5R,6S)-4,5-diacetoxy-6-acetoxymethyl-2-phenoxy-tetrahydro-pyran-3-yl ester

There total 14 articles about Acetic acid (2R,3R,4S,5R,6S)-4,5-diacetoxy-6-acetoxymethyl-2-phenoxy-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: 100.0%

phenyl tetra-O-acetyl-α-L-idopyranoside (39031-66-8) → Acetic acid (2R,3R,4S,5R,6S)-4,5-diacetoxy-6-acetoxymethyl-2-phenoxy-tetrahydro-pyran-3-yl ester (39031-67-9)

Guidance literature:

With 1,1,1,2,2,2-hexamethyldisilane; iodine; In acetonitrile; at 20 ℃; for 3h;

DOI:10.1016/j.carres.2010.02.012

Reference yield: 75.0%

triphenylborane (1095-03-0) + per-O-acetyl-α-D-mannopyranose (4163-65-9) → phenyl α-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside (2872-72-2,3427-45-0,4468-72-8,18463-30-4,30657-71-7,37797-55-0,37797-56-1,39031-66-8,39031-67-9,94798-88-6)

Guidance literature:

ytterbium(III) triflate; at 20 ℃; for 48h;

DOI:10.1016/S0040-4039(01)00644-X

Reference yield: 58.1%

phenol (108-95-2,27073-41-2) + β-D-mannopyranose pentaacetate (83-87-4,604-68-2,604-69-3,2152-77-4,4026-35-1,4163-59-1,4163-60-4,4163-61-5,4163-65-9,4257-94-7,4257-96-9,16299-15-3,19186-39-1,19189-55-0,25878-60-8,25941-03-1,32445-48-0,32445-49-1,32445-53-7,32445-54-8,34685-58-0,34685-59-1,43168-42-9,43168-44-1,43169-22-8,43169-25-1,66966-07-2,70749-17-6,80184-01-6,93221-01-3,93221-02-4,99630-88-3,109215-53-4,115792-70-6,115792-73-9,139894-92-1,139973-25-4,144071-49-8,147648-81-5) → phenyl α-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside (2872-72-2,3427-45-0,4468-72-8,18463-30-4,30657-71-7,37797-55-0,37797-56-1,39031-66-8,39031-67-9,94798-88-6)

Guidance literature:

With tin(IV) chloride; In benzene; for 1h; Mechanism; Heating;

upstream raw materials:

phenol

methyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside

β-D-mannopyranose pentaacetate

per-O-acetyl-α-D-mannopyranose

Downstream raw materials:

phenyl-α-D-talopyranoside

phenyl α-D-mannoopyranoside

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