phenylmethyl-2,3-O-(1-methylethylidene)-5,6-didehydro-5,6-dideoxy-α-D-mannofuranoside

Base Information

• Chemical Name: phenylmethyl-2,3-O-(1-methylethylidene)-5,6-didehydro-5,6-dideoxy-α-D-mannofuranoside
• CAS No.: 74911-90-3
• Molecular Formula: C₁₆H₂₀O₄
• Molecular Weight: 276.332

Synonyms:phenylmethyl-2,3-O-(1-methylethylidene)-5,6-didehydro-5,6-dideoxy-α-D-mannofuranoside

Chemical Property of phenylmethyl-2,3-O-(1-methylethylidene)-5,6-didehydro-5,6-dideoxy-α-D-mannofuranoside

Chemical Property:

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Technology Process of phenylmethyl-2,3-O-(1-methylethylidene)-5,6-didehydro-5,6-dideoxy-α-D-mannofuranoside

There total 3 articles about phenylmethyl-2,3-O-(1-methylethylidene)-5,6-didehydro-5,6-dideoxy-α-D-mannofuranoside 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%

1-O-benzyl-2,3-O-isopropylidene-5,6-di-O-mesyl-α-D-mannofuranose (28978-37-2) → phenylmethyl-2,3-O-(1-methylethylidene)-5,6-didehydro-5,6-dideoxy-α-D-mannofuranoside (74911-90-3)

Guidance literature:

With sodium iodide; In butanone; for 12h; Heating;

DOI:10.1002/hlca.19890720813

Reference yield:

1-O-benzyl-2,3-O-isopropylidene-α-D-manno-furanose (74912-02-0,79940-48-0,94118-99-7,20689-03-6) → phenylmethyl-2,3-O-(1-methylethylidene)-5,6-didehydro-5,6-dideoxy-α-D-mannofuranoside (74911-90-3)

Guidance literature:

Multi-step reaction with 2 steps

1: CH₂Cl₂ / 24 h / Ambient temperature

2: acetic anhydride / 1 h / 130 °C

With acetic anhydride; In dichloromethane;

Reference yield:

phenylmethyl-2,3-O-(1-methylethylidene)-5,6-O-(N,N-dimethylaminomethylene)-α-D-mannofuranoside (78039-06-2) → phenylmethyl-2,3-O-(1-methylethylidene)-5,6-didehydro-5,6-dideoxy-α-D-mannofuranoside (74911-90-3) + Acetic acid (R)-2-acetoxy-1-((3aS,4R,6S,6aS)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-ethyl ester (77988-67-1)

Guidance literature:

With acetic anhydride; at 130 ℃; for 1h; Yield given. Yields of byproduct given;

upstream raw materials:

1-O-benzyl-2,3-O-isopropylidene-5,6-di-O-mesyl-α-D-mannofuranose

phenylmethyl-2,3-O-(1-methylethylidene)-5,6-O-(N,N-dimethylaminomethylene)-α-D-mannofuranoside

1-O-benzyl-2,3-O-isopropylidene-α-D-manno-furanose

Downstream raw materials:

phenylmethyl-2,3-O-(1-methylethylidene)-5-deoxy-α-D-mannofuranoside

phenylmethyl-2,3-O-(1-methylethylidene)-5-deoxy-6-O-methoxymethyl-α-D-mannofuranoside

phenylmethyl-2,3-O-(1-methylethylidene)-5-deoxy-6-O--α-D-mannofuranoside

Benzyl 5-Deoxy-2,3-O-isopropyliden-6-O-(p-toluolsulfonyl)-α-D-mannofuranosid

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