(9S)-3-O-(2,6-anhydro-4-O-benzyl-3-C-methyl-3-O-methyl-2-thio-α-L-altropyranosyl)-9-dihydro-5-O-(2-O-(methoxycarbonyl)-β-D-desosaminyl)erythronolide A N-Oxide

Base Information

• Chemical Name: (9S)-3-O-(2,6-anhydro-4-O-benzyl-3-C-methyl-3-O-methyl-2-thio-α-L-altropyranosyl)-9-dihydro-5-O-(2-O-(methoxycarbonyl)-β-D-desosaminyl)erythronolide A N-Oxide
• CAS No.: 138505-43-8
• Molecular Formula: C₄₆H₇₅NO₁₆S
• Molecular Weight: 930.165
• Mol file: 138505-43-8.mol

Synonyms:(9S)-3-O-(2,6-anhydro-4-O-benzyl-3-C-methyl-3-O-methyl-2-thio-α-L-altropyranosyl)-9-dihydro-5-O-(2-O-(methoxycarbonyl)-β-D-desosaminyl)erythronolide A N-Oxide

Chemical Property of (9S)-3-O-(2,6-anhydro-4-O-benzyl-3-C-methyl-3-O-methyl-2-thio-α-L-altropyranosyl)-9-dihydro-5-O-(2-O-(methoxycarbonyl)-β-D-desosaminyl)erythronolide A N-Oxide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (9S)-3-O-(2,6-anhydro-4-O-benzyl-3-C-methyl-3-O-methyl-2-thio-α-L-altropyranosyl)-9-dihydro-5-O-(2-O-(methoxycarbonyl)-β-D-desosaminyl)erythronolide A N-Oxide

There total 11 articles about (9S)-3-O-(2,6-anhydro-4-O-benzyl-3-C-methyl-3-O-methyl-2-thio-α-L-altropyranosyl)-9-dihydro-5-O-(2-O-(methoxycarbonyl)-β-D-desosaminyl)erythronolide A N-Oxide 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: 66.0%

(9S)-3-O-(2,6-anhydro-4-O-benzyl-3-C-methyl-3-O-methyl-2-thio-α-L-altropyranosyl)-9-dihydro-9,11-O-isopropylidene-5-O-(2-O-(methoxycarbonyl)-β-D-desosaminyl)erythronolide A N-Oxide (138505-42-7) → (9S)-3-O-(2,6-anhydro-4-O-benzyl-3-C-methyl-3-O-methyl-2-thio-α-L-altropyranosyl)-9-dihydro-5-O-(2-O-(methoxycarbonyl)-β-D-desosaminyl)erythronolide A N-Oxide (138505-43-8)

Guidance literature:

With acetic acid; at 40 ℃; for 24h;

DOI:10.1016/0040-4039(91)80777-4

Reference yield:

9S-Dihydroerythronolide A aglycon (15562-19-3,28316-68-9) → (9S)-3-O-(2,6-anhydro-4-O-benzyl-3-C-methyl-3-O-methyl-2-thio-α-L-altropyranosyl)-9-dihydro-5-O-(2-O-(methoxycarbonyl)-β-D-desosaminyl)erythronolide A N-Oxide (138505-43-8)

Guidance literature:

Multi-step reaction with 7 steps

1: 87 percent / DL-10-camphorsulfonic acid / CH₂Cl₂ / 72 h / -30 °C

2: 100 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 1.5 h / 25 °C

3: 95 percent / H₂ / Pd(OH)2/C / ethyl acetate / 2 h / 25 °C

4: 63 percent / silver triflate, 4A molecular sieves / CH₂Cl₂; toluene / 4 h / 25 °C

5: 100 percent / m-chloroperoxybenzoic acid / CH₂Cl₂ / 0.25 h / 25 °C

6: 90 percent / 4A molecular sieves, N-iodosuccinimide, TfOH / CH₂Cl₂ / 0.17 h / -35 °C

7: 66 percent / 50percent aq. AcOH / 12 h / 40 °C

With N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; camphor-10-sulfonic acid; hydrogen; silver trifluoromethanesulfonate; pyridinium p-toluenesulfonate; acetic acid; 3-chloro-benzenecarboperoxoic acid; palladium dihydroxide; In dichloromethane; ethyl acetate; toluene;

DOI:10.1021/ja00118a008

Reference yield:

(9S)-9-dihydro-3,5-O-(p-methoxybenzylidene)erythronolide A (138505-32-5) → (9S)-3-O-(2,6-anhydro-4-O-benzyl-3-C-methyl-3-O-methyl-2-thio-α-L-altropyranosyl)-9-dihydro-5-O-(2-O-(methoxycarbonyl)-β-D-desosaminyl)erythronolide A N-Oxide (138505-43-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 100 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 1.5 h / 25 °C

2: 95 percent / H₂ / Pd(OH)2/C / ethyl acetate / 2 h / 25 °C

3: 63 percent / silver triflate, 4A molecular sieves / CH₂Cl₂; toluene / 4 h / 25 °C

4: 100 percent / m-chloroperoxybenzoic acid / CH₂Cl₂ / 0.25 h / 25 °C

5: 90 percent / 4A molecular sieves, N-iodosuccinimide, TfOH / CH₂Cl₂ / 0.17 h / -35 °C

6: 66 percent / 50percent aq. AcOH / 12 h / 40 °C

With N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; hydrogen; silver trifluoromethanesulfonate; pyridinium p-toluenesulfonate; acetic acid; 3-chloro-benzenecarboperoxoic acid; palladium dihydroxide; In dichloromethane; ethyl acetate; toluene;

DOI:10.1021/ja00118a008

upstream raw materials:

(9S)-3-O-(2,6-anhydro-4-O-benzyl-3-C-methyl-3-O-methyl-2-thio-α-L-altropyranosyl)-9-dihydro-9,11-O-isopropylidene-5-O-(2-O-(methoxycarbonyl)-β-D-desosaminyl)erythronolide A N-Oxide

9S-Dihydroerythronolide A aglycon

(9S)-9-dihydro-9,11-O-isopropylideneerythronolide A

(9S)-9-dihydro-3,5-O-(p-methoxybenzylidene)erythronolide A

Downstream raw materials:

erythromycin

erythromycin A N-oxide