1D-(1,3,5/2,4)-5-acetamido-1-O-<(2S)-2-acetoxy-2-phenylacetyl>-2,3,4-tri-O-(methoxymethyl)cyclopentane-1,2,3,4-tetraol

Base Information

• Chemical Name: 1D-(1,3,5/2,4)-5-acetamido-1-O-<(2S)-2-acetoxy-2-phenylacetyl>-2,3,4-tri-O-(methoxymethyl)cyclopentane-1,2,3,4-tetraol
• CAS No.: 162491-03-4
• Molecular Formula: C₂₃H₃₃NO₁₁
• Molecular Weight: 499.515

Synonyms:1D-(1,3,5/2,4)-5-acetamido-1-O-<(2S)-2-acetoxy-2-phenylacetyl>-2,3,4-tri-O-(methoxymethyl)cyclopentane-1,2,3,4-tetraol

Chemical Property of 1D-(1,3,5/2,4)-5-acetamido-1-O-<(2S)-2-acetoxy-2-phenylacetyl>-2,3,4-tri-O-(methoxymethyl)cyclopentane-1,2,3,4-tetraol

Chemical Property:

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Technology Process of 1D-(1,3,5/2,4)-5-acetamido-1-O-<(2S)-2-acetoxy-2-phenylacetyl>-2,3,4-tri-O-(methoxymethyl)cyclopentane-1,2,3,4-tetraol

There total 3 articles about 1D-(1,3,5/2,4)-5-acetamido-1-O-<(2S)-2-acetoxy-2-phenylacetyl>-2,3,4-tri-O-(methoxymethyl)cyclopentane-1,2,3,4-tetraol 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: 49.1%

(S)-acetylmandelic acid (7322-88-5) + DL-(1,3/2,4,5)-5-acetamido-1,2,3-tri-O-(methoxymethyl)cyclopentane-1,2,3,4-tetraol → 1D-(1,3,5/2,4)-5-acetamido-1-O-<(2S)-2-acetoxy-2-phenylacetyl>-2,3,4-tri-O-(methoxymethyl)cyclopentane-1,2,3,4-tetraol (162491-03-4) + 1L-(1,3,5/2,4)-5-acetamido-1-O-<(2S)-2-acetoxy-2-phenylacetyl>-2,3,4-tri-O-(methoxymethyl)cyclopentane-1,2,3,4-tetraol (162414-00-8)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 ℃; for 0.166667h;

Reference yield:

DL-(1,3,5/2,4)-5-acetamido-1,5-N,O-isopropylidene-2,3,4-tri-O-(methoxymethyl)cyclopentane-1,2,3,4-tetraol → 1D-(1,3,5/2,4)-5-acetamido-1-O-<(2S)-2-acetoxy-2-phenylacetyl>-2,3,4-tri-O-(methoxymethyl)cyclopentane-1,2,3,4-tetraol (162491-03-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 63.8 percent / AcOH / H₂O / 2 h / 60 °C

2: 47.6 percent / DMAP, DCC / CH₂Cl₂ / 0.17 h / 0 °C

With dmap; acetic acid; dicyclohexyl-carbodiimide; In dichloromethane; water;

Reference yield:

DL-(1,3,5/2,4)-5-acetamido-1,5-N,O-isopropylidene-2,3,4-tri-O-acetylcyclopentane-1,2,3,4-tetraol → 1D-(1,3,5/2,4)-5-acetamido-1-O-<(2S)-2-acetoxy-2-phenylacetyl>-2,3,4-tri-O-(methoxymethyl)cyclopentane-1,2,3,4-tetraol (162491-03-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 93.6 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 4 h / Heating

2: 63.8 percent / AcOH / H₂O / 2 h / 60 °C

3: 47.6 percent / DMAP, DCC / CH₂Cl₂ / 0.17 h / 0 °C

With dmap; acetic acid; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; In dichloromethane; water;

upstream raw materials:

(S)-acetylmandelic acid

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