2,4,6-Trimethyl-thiobenzoic acid S-[(2R,3R,6S)-6-[(2R,4S,5R,6S)-5,6-bis-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-dihydro-pyran-(3Z)-ylideneaminooxy]-4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-3,6-dihydro-2H-pyran-3-yl] ester

Base Information

• Chemical Name: 2,4,6-Trimethyl-thiobenzoic acid S-[(2R,3R,6S)-6-[(2R,4S,5R,6S)-5,6-bis-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-dihydro-pyran-(3Z)-ylideneaminooxy]-4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-3,6-dihydro-2H-pyran-3-yl] ester
• CAS No.: 126900-92-3
• Molecular Formula: C₄₈H₆₉NO₈SSi₂
• Molecular Weight: 876.315

Synonyms:2,4,6-Trimethyl-thiobenzoic acid S-[(2R,3R,6S)-6-[(2R,4S,5R,6S)-5,6-bis-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-dihydro-pyran-(3Z)-ylideneaminooxy]-4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-3,6-dihydro-2H-pyran-3-yl] ester

Chemical Property of 2,4,6-Trimethyl-thiobenzoic acid S-[(2R,3R,6S)-6-[(2R,4S,5R,6S)-5,6-bis-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-dihydro-pyran-(3Z)-ylideneaminooxy]-4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-3,6-dihydro-2H-pyran-3-yl] ester

Chemical Property:

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Technology Process of 2,4,6-Trimethyl-thiobenzoic acid S-[(2R,3R,6S)-6-[(2R,4S,5R,6S)-5,6-bis-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-dihydro-pyran-(3Z)-ylideneaminooxy]-4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-3,6-dihydro-2H-pyran-3-yl] ester

There total 13 articles about 2,4,6-Trimethyl-thiobenzoic acid S-[(2R,3R,6S)-6-[(2R,4S,5R,6S)-5,6-bis-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-dihydro-pyran-(3Z)-ylideneaminooxy]-4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-3,6-dihydro-2H-pyran-3-yl] ester 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:

(2R,4S,5R,6S)-5,6-Bis-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-dihydro-pyran-3-one O-[(2S,5R,6R)-4-(tert-butyl-dimethyl-silanyloxy)-5-mercapto-6-methyl-5,6-dihydro-2H-pyran-2-yl]-oxime (126900-91-2) + mesitylene-2-carboxylic acid chloride (938-18-1) → 2,4,6-Trimethyl-thiobenzoic acid S-[(2R,3R,6S)-6-[(2R,4S,5R,6S)-5,6-bis-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-dihydro-pyran-(3Z)-ylideneaminooxy]-4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-3,6-dihydro-2H-pyran-3-yl] ester (126900-92-3)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 25 ℃; for 8h; Yield given;

Reference yield:

Benzoic acid (2R,3R,4R)-4-hydroxy-2-methyl-3,4-dihydro-2H-pyran-3-yl ester (127000-08-2) → 2,4,6-Trimethyl-thiobenzoic acid S-[(2R,3R,6S)-6-[(2R,4S,5R,6S)-5,6-bis-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-dihydro-pyran-(3Z)-ylideneaminooxy]-4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-3,6-dihydro-2H-pyran-3-yl] ester (126900-92-3)

Guidance literature:

Multi-step reaction with 12 steps

1: 55 percent / 55percent m-chloroperoxybenzoic acid, MgSO₄ / CH₂Cl₂ / 0.5 h / 0 °C

2: 67 percent / imidazole / CH₂Cl₂ / 30 h / 25 °C

3: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C to 25 deg C

4: Zn(BH₄)2, NH₄Cl / diethyl ether / 0.33 h / 0 °C

5: diisopropyl azodicarboxylate, Ph₃P / tetrahydrofuran / 0.5 h / 25 °C

6: N₂H₄ / methanol / 0.17 h / 25 °C

7: pyridinium p-toluenesulfonate (PPTS) / benzene / 3 h / 25 °C

8: 99 percent / 2,6-lutidine / 0.5 h / -25 - 0 °C

9: 91 percent / DIBAL / CH₂Cl₂ / 1 h / -78 °C

10: 1.) acetonitrile, 25 deg C, 20 h, 2.) toluene, 110 deg C, 1 h

11: DIBAL / CH₂Cl₂ / 2 h / -78 °C

12: DMAP, Et₃N / CH₂Cl₂ / 8 h / 25 °C

With 1H-imidazole; 2,6-dimethylpyridine; dmap; zinc(II) tetrahydroborate; oxalyl dichloride; di-isopropyl azodicarboxylate; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; magnesium sulfate; ammonium chloride; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; hydrazine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; benzene;

Reference yield:

Benzoic acid (2R,3S,4R)-4-acetoxy-2-methyl-3,4-dihydro-2H-pyran-3-yl ester (126900-82-1) → 2,4,6-Trimethyl-thiobenzoic acid S-[(2R,3R,6S)-6-[(2R,4S,5R,6S)-5,6-bis-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-dihydro-pyran-(3Z)-ylideneaminooxy]-4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-3,6-dihydro-2H-pyran-3-yl] ester (126900-92-3)

Guidance literature:

Multi-step reaction with 13 steps

1: 72 percent / DIBAL / CH₂Cl₂ / 2.5 h / -78 °C

2: 55 percent / 55percent m-chloroperoxybenzoic acid, MgSO₄ / CH₂Cl₂ / 0.5 h / 0 °C

3: 67 percent / imidazole / CH₂Cl₂ / 30 h / 25 °C

4: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C to 25 deg C

5: Zn(BH₄)2, NH₄Cl / diethyl ether / 0.33 h / 0 °C

6: diisopropyl azodicarboxylate, Ph₃P / tetrahydrofuran / 0.5 h / 25 °C

7: N₂H₄ / methanol / 0.17 h / 25 °C

8: pyridinium p-toluenesulfonate (PPTS) / benzene / 3 h / 25 °C

9: 99 percent / 2,6-lutidine / 0.5 h / -25 - 0 °C

10: 91 percent / DIBAL / CH₂Cl₂ / 1 h / -78 °C

11: 1.) acetonitrile, 25 deg C, 20 h, 2.) toluene, 110 deg C, 1 h

12: DIBAL / CH₂Cl₂ / 2 h / -78 °C

13: DMAP, Et₃N / CH₂Cl₂ / 8 h / 25 °C

With 1H-imidazole; 2,6-dimethylpyridine; dmap; zinc(II) tetrahydroborate; oxalyl dichloride; di-isopropyl azodicarboxylate; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; magnesium sulfate; ammonium chloride; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; hydrazine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; benzene;

upstream raw materials:

(2R,4S,5R,6S)-5,6-Bis-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-dihydro-pyran-3-one O-[(2S,5R,6R)-4-(tert-butyl-dimethyl-silanyloxy)-5-mercapto-6-methyl-5,6-dihydro-2H-pyran-2-yl]-oxime

mesitylene-2-carboxylic acid chloride

Benzoic acid (2R,3R,4R)-4-hydroxy-2-methyl-3,4-dihydro-2H-pyran-3-yl ester

Benzoic acid (2R,3S,4R)-4-acetoxy-2-methyl-3,4-dihydro-2H-pyran-3-yl ester

Downstream raw materials:

2,4,6-Trimethyl-thiobenzoic acid S-{(2R,3R,6S)-6-[(2R,4S,5R,6S)-5,6-bis-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-dihydro-pyran-(3Z)-ylideneaminooxy]-2-methyl-4-oxo-tetrahydro-pyran-3-yl} ester

phenylmethyl 4,6-dideoxy-4-<<<2,6-dideoxy-4-S-(2,4,6-trimethylbenzoyl)-4-thio-β-D-ribo-hexopyranosyl>oxy>amino>-2-O-(phenylmethyl)-α-D-glucopyranoside

2,4,6-Trimethyl-thiobenzoic acid S-{(2R,3S,4S,6S)-6-[(2R,4S,5R,6S)-5,6-bis-benzyloxy-4-hydroxy-2-methyl-dihydro-pyran-(3E)-ylideneaminooxy]-4-hydroxy-2-methyl-tetrahydro-pyran-3-yl} ester

2,4,6-Trimethyl-thiobenzoic acid S-{(2R,3S,4S,6S)-6-[(2R,4S,5R,6S)-5,6-bis-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-dihydro-pyran-(3Z)-ylideneaminooxy]-4-hydroxy-2-methyl-tetrahydro-pyran-3-yl} ester

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