phenylmethyl 3,4,6-tri-O-acetyl-2-deoxy-α-D-arabinohexopyranose

Base Information

• Chemical Name: phenylmethyl 3,4,6-tri-O-acetyl-2-deoxy-α-D-arabinohexopyranose
• CAS No.: 79698-05-8
• Molecular Formula: C₁₉H₂₄O₈
• Molecular Weight: 380.395
• Mol file: 79698-05-8.mol

Synonyms:phenylmethyl 3,4,6-tri-O-acetyl-2-deoxy-α-D-arabinohexopyranose

Chemical Property of phenylmethyl 3,4,6-tri-O-acetyl-2-deoxy-α-D-arabinohexopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

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Technology Process of phenylmethyl 3,4,6-tri-O-acetyl-2-deoxy-α-D-arabinohexopyranose

There total 7 articles about phenylmethyl 3,4,6-tri-O-acetyl-2-deoxy-α-D-arabinohexopyranose 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: 87.0%

benzyl alcohol (100-51-6,185532-71-2) + D-glucal triacetate (2873-29-2) → phenylmethyl 3,4,6-tri-O-acetyl-2-deoxy-α-D-arabinohexopyranose (79698-05-8)

Guidance literature:

With cerium(III) chloride; sodium iodide; In acetonitrile; for 8h; Heating;

DOI:10.1016/S0040-4039(02)01584-8

Reference yield: 84.0%

benzyl 3,4,6-tri-O-acetyl-2-bromo-2-deoxy-α-D-mannopyranoside (79698-04-7) → phenylmethyl 3,4,6-tri-O-acetyl-2-deoxy-α-D-arabinohexopyranose (79698-05-8)

Guidance literature:

With hydrogen; triethylamine; nickel; In ethyl acetate;

DOI:10.1016/S0008-6215(00)81880-7

Reference yield:

benzyl alcohol (100-51-6,185532-71-2) + 1,3,4,6-tetra-O-acetyl-2-deoxy-α-D-arabinohexopyranose (16750-06-4) → (2R,3S,4R,6R)-2-(acetoxymethyl)-6-(benzyloxy)tetrahydro-2H-pyran-3,4-diyl diacetate (1385782-82-0) + phenylmethyl 3,4,6-tri-O-acetyl-2-deoxy-α-D-arabinohexopyranose (79698-05-8)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 0.5h; Overall yield = 97 %; Overall yield = 33.2 mg; stereoselective reaction; Inert atmosphere; Molecular sieve;

DOI:10.1080/07328303.2018.1439498

upstream raw materials:

benzyl 3,4,6-tri-O-acetyl-2-bromo-2-deoxy-α-D-mannopyranoside

benzyl alcohol

D-glucal triacetate

(2R,3S,4S,5R,6R)-6-(acetoxymethyl)-3-iodotetrahydro-2H-pyran-2,4,5-triyl triacetate

Downstream raw materials:

benzyl 2-deoxy-α-D-arabino-hexopyranoside