bis(ethyloxy)phosphinoyl-4-<(6-deoxy-3-O-methyl-α-L-mannopyranosyl)oxy>-5-iodo-2,3-dimethoxy-6-methylbenzoate

Base Information

• Chemical Name: bis(ethyloxy)phosphinoyl-4-<(6-deoxy-3-O-methyl-α-L-mannopyranosyl)oxy>-5-iodo-2,3-dimethoxy-6-methylbenzoate
• CAS No.: 153693-30-2
• Molecular Formula: C₂₁H₃₂IO₁₂P
• Molecular Weight: 634.356

Synonyms:bis(ethyloxy)phosphinoyl-4-<(6-deoxy-3-O-methyl-α-L-mannopyranosyl)oxy>-5-iodo-2,3-dimethoxy-6-methylbenzoate

Chemical Property of bis(ethyloxy)phosphinoyl-4-<(6-deoxy-3-O-methyl-α-L-mannopyranosyl)oxy>-5-iodo-2,3-dimethoxy-6-methylbenzoate

Chemical Property:

Purity/Quality:

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Technology Process of bis(ethyloxy)phosphinoyl-4-<(6-deoxy-3-O-methyl-α-L-mannopyranosyl)oxy>-5-iodo-2,3-dimethoxy-6-methylbenzoate

There total 13 articles about bis(ethyloxy)phosphinoyl-4-<(6-deoxy-3-O-methyl-α-L-mannopyranosyl)oxy>-5-iodo-2,3-dimethoxy-6-methylbenzoate 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: 51.0%

diethyl chlorophosphate (814-49-3) + 4-(6-Deoxy-3-O-methyl-α-L-mannopyranosyloxy)-3-iodo-5,6-dimethoxy-2-methylbenzoic acid (153693-58-4) → bis(ethyloxy)phosphinoyl-4-<(6-deoxy-3-O-methyl-α-L-mannopyranosyl)oxy>-5-iodo-2,3-dimethoxy-6-methylbenzoate (153693-30-2)

Guidance literature:

With triethylamine; In tetrahydrofuran; at 25 ℃; for 0.333333h;

DOI:10.1021/ja00084a018

Reference yield:

4-Hydroxy-5-iod-2,3-dimethoxy-6-methyl-benzoesaeuremethylester (115592-74-0,115650-45-8,127761-05-1) → bis(ethyloxy)phosphinoyl-4-<(6-deoxy-3-O-methyl-α-L-mannopyranosyl)oxy>-5-iodo-2,3-dimethoxy-6-methylbenzoate (153693-30-2)

Guidance literature:

Multi-step reaction with 7 steps

1: DIBAL / CH₂Cl₂ / 1.) -78 deg C, 10 min, 2.) 25 deg C, 5 min

2: imidazole / dimethylformamide / 2 h / 65 °C

3: 1.) 2,6-di-tert-butyl-4-methylpyridine, 2.) (Bu₃Sn)2O

4: 84 percent / TBAF / tetrahydrofuran / 4 h / 25 °C

5: 79 percent / NaIO₄, RuCl₃ / CCl₄; acetonitrile; H₂O / 1.) 0 deg C, 1 h, 2.) 25 deg C, 1.5 h

6: 84 percent / LiOH / tetrahydrofuran; H₂O / 24 h / 25 °C

7: 51 percent / Et₃N / tetrahydrofuran / 0.33 h / 25 °C

With 1H-imidazole; ruthenium trichloride; lithium hydroxide; sodium periodate; 2,6-di-tert-butyl-4-methylpyridine; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; triethylamine; bis(tri-n-butyltin)oxide; In tetrahydrofuran; tetrachloromethane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ja00084a018

Reference yield:

phenyl 1-thio-α-L-rhamnopyranose (1214-98-8,105026-40-2,127061-11-4,131724-82-8) → bis(ethyloxy)phosphinoyl-4-<(6-deoxy-3-O-methyl-α-L-mannopyranosyl)oxy>-5-iodo-2,3-dimethoxy-6-methylbenzoate (153693-30-2)

Guidance literature:

Multi-step reaction with 11 steps

1: ZnCl₂, 85percent H₃PO₄ / 24 h / 25 °C

2: pyridine / 10 h / 25 °C

3: AcOH, H₂O / tetrahydrofuran / 48 h / 70 °C

4: 1.) 4-A sieves, Bu₂SnO / 1.) DMF, 80 deg C, 5 h, 2.) DMF, 80 deg C, 6 h

5: 82 percent / pyridine / 6 h / 60 °C

6: 92 percent / mCPBA / CH₂Cl₂ / 0.83 h / -78 - 0 °C

7: 1.) 2,6-di-tert-butyl-4-methylpyridine, 2.) (Bu₃Sn)2O

8: 84 percent / TBAF / tetrahydrofuran / 4 h / 25 °C

9: 79 percent / NaIO₄, RuCl₃ / CCl₄; acetonitrile; H₂O / 1.) 0 deg C, 1 h, 2.) 25 deg C, 1.5 h

10: 84 percent / LiOH / tetrahydrofuran; H₂O / 24 h / 25 °C

11: 51 percent / Et₃N / tetrahydrofuran / 0.33 h / 25 °C

With pyridine; ruthenium trichloride; lithium hydroxide; sodium periodate; 2,6-di-tert-butyl-4-methylpyridine; phosphoric acid; 4 A molecular sieve; tetrabutyl ammonium fluoride; water; di(n-butyl)tin oxide; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; bis(tri-n-butyltin)oxide; zinc(II) chloride; In tetrahydrofuran; tetrachloromethane; dichloromethane; water; acetonitrile;

DOI:10.1021/ja00084a018

upstream raw materials:

diethyl chlorophosphate

4-(6-Deoxy-3-O-methyl-α-L-mannopyranosyloxy)-3-iodo-5,6-dimethoxy-2-methylbenzoic acid

4-Hydroxy-5-iod-2,3-dimethoxy-6-methyl-benzoesaeuremethylester

phenyl 1-thio-α-L-rhamnopyranose

Downstream raw materials:

methyl 4,6-dideoxy-4-<<<2,6-dideoxy-4-S-<4-<<3-O-methyl-α-L-rhamnopyranosyl>oxy>-5-iodo-2,3-dimethoxy-6-methylbenzoyl>-4-thio-β-D-ribo-hexopyranosyl>oxy>amino>-2-O-<2,4-dideoxy-4-(ethylamino)-3-O-methyl-α-L-threo-pentopyranosyl>-β-D-glucopyranoside

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