methyl 4,6-O-(phenylmethylene)-3-deoxy-2-O-benzoyl-3-(4-morpholinyl)-α-D-altro-pyranoside

Base Information

• Chemical Name: methyl 4,6-O-(phenylmethylene)-3-deoxy-2-O-benzoyl-3-(4-morpholinyl)-α-D-altro-pyranoside
• CAS No.: 256455-99-9
• Molecular Formula: C₂₅H₂₉NO₇
• Molecular Weight: 455.508

Synonyms:methyl 4,6-O-(phenylmethylene)-3-deoxy-2-O-benzoyl-3-(4-morpholinyl)-α-D-altro-pyranoside

Chemical Property of methyl 4,6-O-(phenylmethylene)-3-deoxy-2-O-benzoyl-3-(4-morpholinyl)-α-D-altro-pyranoside

Chemical Property:

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Technology Process of methyl 4,6-O-(phenylmethylene)-3-deoxy-2-O-benzoyl-3-(4-morpholinyl)-α-D-altro-pyranoside

There total 2 articles about methyl 4,6-O-(phenylmethylene)-3-deoxy-2-O-benzoyl-3-(4-morpholinyl)-α-D-altro-pyranoside 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: 84.0%

benzoyl chloride (98-88-4) + methyl 4,6-O-(phenylmethylene)-3-deoxy-3-(4-morpholinyl)-α-D-altro-pyranoside (256455-94-4) → methyl 4,6-O-(phenylmethylene)-3-deoxy-2-O-benzoyl-3-(4-morpholinyl)-α-D-altro-pyranoside (256455-99-9)

Guidance literature:

methyl 4,6-O-(phenylmethylene)-3-deoxy-3-(4-morpholinyl)-α-D-altro-pyranoside; With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 0.5h;

benzoyl chloride; With pyridine; at 0 ℃; for 2h;

DOI:10.1021/jo982199s

Reference yield:

methyl 2,3-anhydro-4,6-O-benzilidene-α-D-mannopyranoside (3150-15-0,3150-16-1,3257-59-8,14187-71-4,15384-57-3,19465-13-5,32976-15-1,52885-37-7,53270-02-3,53270-03-4,65391-11-9,65391-12-0,66537-92-6,67226-04-4,71184-14-0,86420-78-2,86420-79-3,91177-51-4,91177-52-5,117708-93-7,120408-72-2,2880-96-8) → methyl 4,6-O-(phenylmethylene)-3-deoxy-2-O-benzoyl-3-(4-morpholinyl)-α-D-altro-pyranoside (256455-99-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 89 percent / 10 h / 90 - 100 °C

2.1: NaH / dimethylformamide / 0.5 h / 20 °C

2.2: 84 percent / pyridine / 2 h / 0 °C

With sodium hydride; In N,N-dimethyl-formamide; 1.1: Ring cleavage / 2.1: deprotonation / 2.2: Acylation;

DOI:10.1021/jo982199s

Reference yield:

methyl 4,6-O-(phenylmethylene)-3-deoxy-2-O-benzoyl-3-(4-morpholinyl)-α-D-altro-pyranoside (256455-99-9) → Benzoic acid (2R,4aR,6S,7S,8R,8aS)-6-methoxy-8-(4-oxy-morpholin-4-yl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1021/jo982199s

upstream raw materials:

benzoyl chloride

methyl 4,6-O-(phenylmethylene)-3-deoxy-3-(4-morpholinyl)-α-D-altro-pyranoside

methyl 2,3-anhydro-4,6-O-benzilidene-α-D-mannopyranoside

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