N-9-fluorenylmethyloxycarbonyl 1-2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl> hydroxyproline methyl ester

Base Information

• Chemical Name: N-9-fluorenylmethyloxycarbonyl 1-2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl> hydroxyproline methyl ester
• CAS No.: 122350-60-1
• Molecular Formula: C₅₅H₅₅NO₁₀
• Molecular Weight: 890.042

Synonyms:

Chemical Property of N-9-fluorenylmethyloxycarbonyl 1-2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl> hydroxyproline methyl ester

Chemical Property:

Purity/Quality:

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Technology Process of N-9-fluorenylmethyloxycarbonyl 1-2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl> hydroxyproline methyl ester

There total 2 articles about N-9-fluorenylmethyloxycarbonyl 1-2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl> hydroxyproline methyl 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: 40.0%

2,3,4,6-Tetra-O-benzyl-D-glucopyranose (4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5,4132-28-9) + (2S,4R)-1-(9H-fluoren-9-yl)methyl-2-methyl-4-hydroxypyrrolidine-1,2-dicarboxylate (122350-59-8) → N-9-fluorenylmethyloxycarbonyl 1-2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl> hydroxyproline methyl ester (122350-60-1,122407-74-3) + N-9-fluorenylmethyloxycarbonyl 1-2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl> hydroxyproline methyl ester (122350-60-1,122407-74-3)

Guidance literature:

With trifluoromethylsulfonic anhydride; In dichloromethane; -70 deg C, 5 min then R_.T_., 1 h;

DOI:10.1016/S0040-4020(01)89802-1

Reference yield: 40.0%

2,3,4,6-Tetra-O-benzyl-D-glucopyranose (4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5,4132-28-9) + (2S,4R)-1-(9H-fluoren-9-yl)methyl-2-methyl-4-hydroxypyrrolidine-1,2-dicarboxylate (122350-59-8) → N-9-fluorenylmethyloxycarbonyl 1-2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl> hydroxyproline methyl ester (122350-60-1,122407-74-3) + N-9-fluorenylmethyloxycarbonyl 1-2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl> hydroxyproline methyl ester (122350-60-1,122407-74-3)

Guidance literature:

With trifluoromethylsulfonic anhydride; In dichloromethane; -70 deg C, 5 min then R_.T_., 1 h;

DOI:10.1016/S0040-4020(01)89802-1

Reference yield:

N-9-fluorenylmethyloxycarbonyl 1-2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl> hydroxyproline methyl ester (122350-60-1,122407-74-3) → (2S,4R)-4-((2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-pyrrolidine-2-carboxylic acid methyl ester

Guidance literature:

With piperidine; In dichloromethane; for 1h; Ambient temperature;

DOI:10.1016/S0040-4020(01)89802-1

upstream raw materials:

2,3,4,6-Tetra-O-benzyl-D-glucopyranose

(2S,4R)-1-(9H-fluoren-9-yl)methyl-2-methyl-4-hydroxypyrrolidine-1,2-dicarboxylate

Downstream raw materials:

Boc-Tyr-DMet-Gly-Phe-1-2,3,4,6-tetra-O-benzyl-β-glcp> Hyp-OMe

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