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

Base Information

• Chemical Name: 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
• CAS No.: 126900-94-5
• Molecular Formula: C₄₂H₅₇NO₈SSi
• Molecular Weight: 764.068

Synonyms: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

Chemical Property of 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

Chemical Property:

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Safty Information:

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Technology Process of 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

There total 16 articles about 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 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:

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 (126900-93-4) → 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 (126900-94-5)

Guidance literature:

With potassium tri-sec-butyl-borohydride; In 1,2-dimethoxyethane; at -78 ℃; for 1.5h; Yield given;

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,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 (126900-94-5)

Guidance literature:

Multi-step reaction with 15 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

14: n-Bu₄NF (TBAF) / tetrahydrofuran; H₂O; acetic acid / 0.33 h / 0 °C

15: K-Selectride / 1,2-dimethoxy-ethane / 1.5 h / -78 °C

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

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,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 (126900-94-5)

Guidance literature:

Multi-step reaction with 14 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

13: n-Bu₄NF (TBAF) / tetrahydrofuran; H₂O; acetic acid / 0.33 h / 0 °C

14: K-Selectride / 1,2-dimethoxy-ethane / 1.5 h / -78 °C

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

upstream 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

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

(2R)-trans-4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-3,6-dihydro-6-methyl-3-oxo-2H-pyran-2-yl 3-chlorobenzoate

Downstream raw materials:

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

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

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