dibutyl 2-O-acetyl-3,4-di-O-benzyl-6-O-(9-fluorenylmethoxycarbonyl)-α-D-mannopyranoside phosphate

Base Information

• Chemical Name: dibutyl 2-O-acetyl-3,4-di-O-benzyl-6-O-(9-fluorenylmethoxycarbonyl)-α-D-mannopyranoside phosphate
• CAS No.: 943837-16-9
• Molecular Formula: C₄₅H₅₃O₁₂P
• Molecular Weight: 816.882

Synonyms:dibutyl 2-O-acetyl-3,4-di-O-benzyl-6-O-(9-fluorenylmethoxycarbonyl)-α-D-mannopyranoside phosphate

Chemical Property of dibutyl 2-O-acetyl-3,4-di-O-benzyl-6-O-(9-fluorenylmethoxycarbonyl)-α-D-mannopyranoside phosphate

Chemical Property:

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Technology Process of dibutyl 2-O-acetyl-3,4-di-O-benzyl-6-O-(9-fluorenylmethoxycarbonyl)-α-D-mannopyranoside phosphate

There total 1 articles about dibutyl 2-O-acetyl-3,4-di-O-benzyl-6-O-(9-fluorenylmethoxycarbonyl)-α-D-mannopyranoside phosphate 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%

dibutyl (2-O-acetyl-3,4-di-O-benzyl-α-D-mannopyranosyl) phosphate (943837-13-6) + (fluorenylmethoxy)carbonyl chloride (28920-43-6) → dibutyl 2-O-acetyl-3,4-di-O-benzyl-6-O-(9-fluorenylmethoxycarbonyl)-α-D-mannopyranoside phosphate (943837-16-9)

Guidance literature:

With pyridine; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1080/07328300701298204

Reference yield: 89.0%

dibutyl 2-O-acetyl-3,4-di-O-benzyl-6-O-(9-fluorenylmethoxycarbonyl)-α-D-mannopyranoside phosphate (943837-16-9) + pent-4-enyl 3,4-di-O-benzyl-2-O-pivaloyl-β-D-glucopyranoside (960205-32-7) → pent-4-enyl 2-O-acetyl-3,4-di-O-benzyl-6-O-(fluorenylmethoxycarbonyl)-α-D-mannopyranosyl-(1->6)-3,4-di-O-benzyl-2-O-pivaloyl-β-D-glucopyranoside (960205-36-1)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane; at -30 ℃; for 0.25h;

DOI:10.1021/jo701349c

Reference yield:

dibutyl 3,4-di-O-benzyl-6-O-(9-fluorenylmethoxycarbonyl)-2-O-pivaloyl-β-D-glucopyranoside phosphate (943439-96-1) + 8-(4,4'-dimethoxytrityloxy)oct-4(Z)-en-1-ol (253683-39-5) + dibutyl 2-O-acetyl-3,4-di-O-benzyl-6-O-(9-fluorenylmethoxycarbonyl)-α-D-mannopyranoside phosphate (943837-16-9) + acetic anhydride (108-24-7) + diisopropyl-(1H,1H,2H,2H-perfluorodecyl)silyl triflate (404942-40-1) → pent-4-enyl 6-O-acetyl-3,4-di-O-benzyl-2-O-pivaloyl-β-D-glucopyranoside (960205-34-9) + pent-4-enyl 3,4-di-O-benzyl-6-O-{(1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8-heptadecafluorodecyl)diisopropylsilyl}-2-O-pivaloyl-β-D-glucopyranosyl-(1->6)-2-O-acetyl-3,4-di-O-benzyl-α-D-mannopyranosyl-(1->6)-3,4-di-O-benzyl-2-O-pivaloyl-β-D-glucopyranoside

Guidance literature:

Multistep reaction.;

DOI:10.1021/jo701349c

upstream raw materials:

dibutyl (2-O-acetyl-3,4-di-O-benzyl-α-D-mannopyranosyl) phosphate

(fluorenylmethoxy)carbonyl chloride

Downstream raw materials:

pent-4-enyl 6-O-acetyl-3,4-di-O-benzyl-2-O-pivaloyl-β-D-glucopyranoside

pent-4-enyl 2-O-acetyl-3,4-di-O-benzyl-6-O-(fluorenylmethoxycarbonyl)-α-D-mannopyranosyl-(1->6)-3,4-di-O-benzyl-2-O-pivaloyl-β-D-glucopyranoside

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