Methyl-4-O-benzoyl-3-(benzoylamino)-2,3,6-tridesoxy-3-C-methyl-α-L-lyxo-hexopyranosid

Base Information

Chemical Name:Methyl-4-O-benzoyl-3-(benzoylamino)-2,3,6-tridesoxy-3-C-methyl-α-L-lyxo-hexopyranosid
CAS No.:37091-13-7
Molecular Formula:C₂₂H₂₅NO₅
Molecular Weight:383.444
Hs Code.:

Synonyms:Methyl-4-O-benzoyl-3-(benzoylamino)-2,3,6-tridesoxy-3-C-methyl-α-L-lyxo-hexopyranosid

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Chemical Property of Methyl-4-O-benzoyl-3-(benzoylamino)-2,3,6-tridesoxy-3-C-methyl-α-L-lyxo-hexopyranosid

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Technology Process of Methyl-4-O-benzoyl-3-(benzoylamino)-2,3,6-tridesoxy-3-C-methyl-α-L-lyxo-hexopyranosid

There total 15 articles about Methyl-4-O-benzoyl-3-(benzoylamino)-2,3,6-tridesoxy-3-C-methyl-α-L-lyxo-hexopyranosid 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: 79.0%

: 98-88-4
benzoyl chloride

: 37091-12-6
methyl 3-amino-2,3,6-trideoxy-3-C-methyl-α-L-lyxo-hexopyranoside

: 37091-13-7
Methyl-4-O-benzoyl-3-(benzoylamino)-2,3,6-tridesoxy-3-C-methyl-α-L-lyxo-hexopyranosid

Guidance literature:: In pyridine;
DOI:10.1016/S0008-6215(00)80859-9

Reference yield:

: 67974-22-5,71695-40-4,71695-43-7,72209-37-1,76172-88-8,78910-47-1,83158-18-3,83158-20-7,84373-99-9,85687-28-1
methyl 3-acetamido-2,3,6-trideoxy-3-C-methyl-α-L-arabino-hexopyranoside

: 37091-13-7
Methyl-4-O-benzoyl-3-(benzoylamino)-2,3,6-tridesoxy-3-C-methyl-α-L-lyxo-hexopyranosid

Guidance literature:: Multi-step reaction with 4 steps

1: 66 percent / pyridinium chlorochromate / 3 Angstroem molecular sieves / CH₂Cl₂ / 3 h / Ambient temperature

2: 80 percent / L-Selectride / tetrahydrofuran / 1.) -15 deg C, 1 h; 2.) room temperature

3: 62 percent / barium hydroxide octahydrate / H₂O / 24 h / Heating

4: 79 percent / pyridine

With barium hydroxide octahydrate; L-Selectride; pyridinium chlorochromate; 3 A molecular sieve; In tetrahydrofuran; pyridine; dichloromethane; water;
DOI:10.1016/S0008-6215(00)80859-9

Reference yield:

: 61199-73-3
methyl 2,3-O-benzylidene-6-deoxy-α-L-mannopyranoside

: 37091-13-7
Methyl-4-O-benzoyl-3-(benzoylamino)-2,3,6-tridesoxy-3-C-methyl-α-L-lyxo-hexopyranosid

Guidance literature:: Multi-step reaction with 9 steps

2.1: DMAP / methanol

2.2: H⁺ / methanol

3.1: ion exchange resin

4.1: 61 percent / PPh₃; diethyl azodicarboxylate / tetrahydrofuran / 18 h / 20 °C

5.1: 85 percent / Amberlite IRA 400 (OH) resin / methanol / 30 h / 20 °C

6.1: 90 percent / NaH / kerosene / 0.5 h / 20 °C

7.1: mercury(II) trifluoroacetate / tetrahydrofuran / 20 h / 20 °C

7.2: 96 percent / sodium borohydride / aq. NaOH / 2 h / 0 °C / pH 12

8.1: 93 percent / Ba(OH)2 / H₂O / 22 h / Heating

9.1: 62 percent / pyridine / 20 h / 20 °C

With dmap; barium dihydroxide; Amberlite IRA 400 (OH) resin; ion exchange resin; mercury(II) trifluoroacetate; sodium hydride; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; pyridine; methanol; water; kerosene; 1.1: Methylation / 2.1: Acetylation / 2.2: Rearrangement / 3.1: Deacetylation / 4.1: Substitution / 5.1: Elimination / 6.1: Substitution / 7.1: Cyclization / 7.2: Reduction / 8.1: Hydrolysis / 9.1: benzoylation;
DOI:10.1016/S0008-6215(99)00259-1