allyl 3,6-di-O-benzyl-4-O-(9-fluorenylmethoxycarbonyl)-2-O-levulinoyl-α-L-idopyranoside

Base Information

• Chemical Name: allyl 3,6-di-O-benzyl-4-O-(9-fluorenylmethoxycarbonyl)-2-O-levulinoyl-α-L-idopyranoside
• CAS No.: 647027-47-2
• Molecular Formula: C₄₃H₄₄O₁₀
• Molecular Weight: 720.816

Synonyms:allyl 3,6-di-O-benzyl-4-O-(9-fluorenylmethoxycarbonyl)-2-O-levulinoyl-α-L-idopyranoside

Chemical Property of allyl 3,6-di-O-benzyl-4-O-(9-fluorenylmethoxycarbonyl)-2-O-levulinoyl-α-L-idopyranoside

Chemical Property:

Purity/Quality:

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Technology Process of allyl 3,6-di-O-benzyl-4-O-(9-fluorenylmethoxycarbonyl)-2-O-levulinoyl-α-L-idopyranoside

There total 2 articles about allyl 3,6-di-O-benzyl-4-O-(9-fluorenylmethoxycarbonyl)-2-O-levulinoyl-α-L-idopyranoside 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: 89.0%

levulinic acid (123-76-2) + allyl 3,6-di-O-benzyl-4-O-(9-fluorenylmethoxycarbonyl)-α-L-idopyranoside (647027-46-1) → allyl 3,6-di-O-benzyl-4-O-(9-fluorenylmethoxycarbonyl)-2-O-levulinoyl-α-L-idopyranoside (647027-47-2)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 8h;

DOI:10.1021/ol0359261

Reference yield:

allyl 2-O-acetyl-3,6-di-O-benzyl-4-O-(9-fluorenylmethoxycarbonyl)-α-L-idopyranoside (647027-45-0) → allyl 3,6-di-O-benzyl-4-O-(9-fluorenylmethoxycarbonyl)-2-O-levulinoyl-α-L-idopyranoside (647027-47-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / acetyl chloride / methanol / 6 h / 0 - 20 °C

2: 89 percent / dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / CH₂Cl₂ / 8 h / 20 °C

With dmap; acetyl chloride; dicyclohexyl-carbodiimide; In methanol; dichloromethane;

DOI:10.1021/ol0359261

Reference yield: 82.0%

allyl 3,6-di-O-benzyl-4-O-(9-fluorenylmethoxycarbonyl)-2-O-levulinoyl-α-L-idopyranoside (647027-47-2) → 3,6-di-O-benzyl-4-O-(9-fluorenylmethoxycarbonyl)-2-O-levulinoyl-α,β-L-idopyranose

Guidance literature:

With Wilkinson's catalyst; In ethanol; water; toluene; for 15h; Heating;

DOI:10.1021/ol0359261

upstream raw materials:

levulinic acid

allyl 3,6-di-O-benzyl-4-O-(9-fluorenylmethoxycarbonyl)-α-L-idopyranoside

allyl 2-O-acetyl-3,6-di-O-benzyl-4-O-(9-fluorenylmethoxycarbonyl)-α-L-idopyranoside

Downstream raw materials:

allyl 2-azido-2-deoxy-3-O-benzyl-4-O-[(3,6-di-O-benzyl-4-O-(9-fluorenylmethoxycarbonyl)-2-O-levulinoyl-α-L-idopyranosyl)]-β-D-glucopyranoside

allyl 2-azido-2-deoxy-3-O-benzyl-6-O-tertbutyldiphenylsilyl-4-O-[(3,6-di-O-benzyl-4-O-(9-fluorenylmethoxycarbonyl)-α-L-idopyranosyl)]-β-D-glucopyranoside

allyl 2-azido-2-deoxy-3-O-benzyl-6-O-tertbutyldiphenylsilyl-4-O-[(3,6-di-O-benzyl-4-O-(9-fluorenylmethoxycarbonyl)-2-O-levulinoyl-α-L-idopyranosyl)]-β-D-glucopyranoside

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