4-Benzyloxy-3,5-dichloro-2-methoxy-6-methyl-benzoic acid (2R,3R,4R,6S)-6-((2R,3R,4S,5R)-5,6-diacetoxy-4-benzyloxy-2-methyl-tetrahydro-pyran-3-yloxy)-2-methyl-4-triisopropylsilanyloxy-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: 4-Benzyloxy-3,5-dichloro-2-methoxy-6-methyl-benzoic acid (2R,3R,4R,6S)-6-((2R,3R,4S,5R)-5,6-diacetoxy-4-benzyloxy-2-methyl-tetrahydro-pyran-3-yloxy)-2-methyl-4-triisopropylsilanyloxy-tetrahydro-pyran-3-yl ester
• CAS No.: 256327-66-9
• Molecular Formula: C₄₈H₆₄Cl₂O₁₃Si
• Molecular Weight: 948.02

Synonyms:4-Benzyloxy-3,5-dichloro-2-methoxy-6-methyl-benzoic acid (2R,3R,4R,6S)-6-((2R,3R,4S,5R)-5,6-diacetoxy-4-benzyloxy-2-methyl-tetrahydro-pyran-3-yloxy)-2-methyl-4-triisopropylsilanyloxy-tetrahydro-pyran-3-yl ester

Chemical Property of 4-Benzyloxy-3,5-dichloro-2-methoxy-6-methyl-benzoic acid (2R,3R,4R,6S)-6-((2R,3R,4S,5R)-5,6-diacetoxy-4-benzyloxy-2-methyl-tetrahydro-pyran-3-yloxy)-2-methyl-4-triisopropylsilanyloxy-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-Benzyloxy-3,5-dichloro-2-methoxy-6-methyl-benzoic acid (2R,3R,4R,6S)-6-((2R,3R,4S,5R)-5,6-diacetoxy-4-benzyloxy-2-methyl-tetrahydro-pyran-3-yloxy)-2-methyl-4-triisopropylsilanyloxy-tetrahydro-pyran-3-yl ester

There total 42 articles about 4-Benzyloxy-3,5-dichloro-2-methoxy-6-methyl-benzoic acid (2R,3R,4R,6S)-6-((2R,3R,4S,5R)-5,6-diacetoxy-4-benzyloxy-2-methyl-tetrahydro-pyran-3-yloxy)-2-methyl-4-triisopropylsilanyloxy-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: 98.0%

acetic anhydride (108-24-7) + 4-Benzyloxy-3,5-dichloro-2-methoxy-6-methyl-benzoic acid (2R,3R,4R,6S)-6-((2R,3R,4R,5R)-4-benzyloxy-5,6-dihydroxy-2-methyl-tetrahydro-pyran-3-yloxy)-2-methyl-4-triisopropylsilanyloxy-tetrahydro-pyran-3-yl ester → 4-Benzyloxy-3,5-dichloro-2-methoxy-6-methyl-benzoic acid (2R,3R,4R,6S)-6-((2R,3R,4S,5R)-5,6-diacetoxy-4-benzyloxy-2-methyl-tetrahydro-pyran-3-yloxy)-2-methyl-4-triisopropylsilanyloxy-tetrahydro-pyran-3-yl ester (256327-66-9)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 0 - 25 ℃; for 1h;

DOI:10.1002/(SICI)1521-3773(19991115)38:22<3334::AID-ANIE3334>3.0.CO;2-H

Reference yield:

orcinol (504-15-4) → 4-Benzyloxy-3,5-dichloro-2-methoxy-6-methyl-benzoic acid (2R,3R,4R,6S)-6-((2R,3R,4S,5R)-5,6-diacetoxy-4-benzyloxy-2-methyl-tetrahydro-pyran-3-yloxy)-2-methyl-4-triisopropylsilanyloxy-tetrahydro-pyran-3-yl ester (256327-66-9)

Guidance literature:

Multi-step reaction with 18 steps

1.1: AlCl₃; HCl / 3 h / 0 °C

1.2: 92 percent / H₂O / 0.5 h / 0 - 100 °C

2.1: 80 percent / NaClO₂; NaH₂PO₄ / dimethylsulfoxide / 12 h / 0 °C

3.1: 90 percent / NaHCO₃ / CH₂Cl₂ / 12 h / 25 °C

4.1: 95 percent / SO₂Cl₂ / CH₂Cl₂ / 3 h / 35 °C

5.1: 90 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

6.1: 91 percent / Ag₂O / diethyl ether / 12 h / 30 °C

7.1: 96 percent / n-Bu₄NF / tetrahydrofuran / 2 h / 25 °C

8.1: 92 percent / K₂CO₃ / acetone / 70 °C

9.1: 90 percent / DIBAL / CH₂Cl₂ / 1 h / -78 °C

10.1: 90 percent / PDC; molecular sieves 3 Angstroem / CH₂Cl₂ / 3 h / 25 °C

11.1: 95 percent / NaClO₂; NaH₂PO₄; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H₂O / 3 h / 25 °C

12.1: 97 percent / (Me₂N)2CF(+)*PF₆(-); (i-Pr)2NEt / CH₂Cl₂ / 2 h / 0 - 25 °C

13.1: n-BuLi / tetrahydrofuran / 1 h / -78 - 0 °C

13.2: 99 percent / tetrahydrofuran / 25 °C

14.1: DABCO / [(Ph₃P)RhCl] / aq. ethanol / 2 h / 90 °C

15.1: NMO; OsO₄; H₂O / acetone / 8 h / 25 °C

16.1: 93 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 - 25 °C

17.1: 83 percent / PhSH; BF₃*OEt₂ / CH₂Cl₂ / 2 h / -30 °C

18.1: 98 percent / NEt₃; 4-DMAP / CH₂Cl₂ / 1 h / 0 - 25 °C

With 1,4-diaza-bicyclo[2.2.2]octane; 2,6-dimethylpyridine; hydrogenchloride; dmap; sodium chlorite; sodium dihydrogenphosphate; osmium(VIII) oxide; dipyridinium dichromate; n-butyllithium; aluminium trichloride; sulfuryl dichloride; N-methyl-2-indolinone; 2-methyl-but-2-ene; 3 A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; water; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; thiophenol; triethylamine; N-ethyl-N,N-diisopropylamine; fluoro-N,N,N',N'-tetramethylformamidinium hexafluorophosphate; silver(l) oxide; Wilkinson's catalyst; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; dimethyl sulfoxide; acetone; tert-butyl alcohol; 1.1: Formylation / 1.2: Hydrolysis / 2.1: Oxidation / 3.1: Methylation / 4.1: Chlorination / 5.1: Etherification / 6.1: Methylation / 7.1: Desilylation / 8.1: Etherification / 9.1: Reduction / 10.1: Oxidation / 11.1: Oxidation / 12.1: Substitution / 13.1: Metallation / 13.2: Esterification / 14.1: Isomerization / 15.1: Oxidation / 16.1: Etherification / 17.1: Dealkylation / 18.1: Acetylation;

DOI:10.1002/(SICI)1521-3773(19991115)38:22<3334::AID-ANIE3334>3.0.CO;2-H

Reference yield:

2,4-dihydroxy-6-methylbenzaldehyde (487-69-4) → 4-Benzyloxy-3,5-dichloro-2-methoxy-6-methyl-benzoic acid (2R,3R,4R,6S)-6-((2R,3R,4S,5R)-5,6-diacetoxy-4-benzyloxy-2-methyl-tetrahydro-pyran-3-yloxy)-2-methyl-4-triisopropylsilanyloxy-tetrahydro-pyran-3-yl ester (256327-66-9)

Guidance literature:

Multi-step reaction with 17 steps

1.1: 80 percent / NaClO₂; NaH₂PO₄ / dimethylsulfoxide / 12 h / 0 °C

2.1: 90 percent / NaHCO₃ / CH₂Cl₂ / 12 h / 25 °C

3.1: 95 percent / SO₂Cl₂ / CH₂Cl₂ / 3 h / 35 °C

4.1: 90 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

5.1: 91 percent / Ag₂O / diethyl ether / 12 h / 30 °C

6.1: 96 percent / n-Bu₄NF / tetrahydrofuran / 2 h / 25 °C

7.1: 92 percent / K₂CO₃ / acetone / 70 °C

8.1: 90 percent / DIBAL / CH₂Cl₂ / 1 h / -78 °C

9.1: 90 percent / PDC; molecular sieves 3 Angstroem / CH₂Cl₂ / 3 h / 25 °C

10.1: 95 percent / NaClO₂; NaH₂PO₄; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H₂O / 3 h / 25 °C

11.1: 97 percent / (Me₂N)2CF(+)*PF₆(-); (i-Pr)2NEt / CH₂Cl₂ / 2 h / 0 - 25 °C

12.1: n-BuLi / tetrahydrofuran / 1 h / -78 - 0 °C

12.2: 99 percent / tetrahydrofuran / 25 °C

13.1: DABCO / [(Ph₃P)RhCl] / aq. ethanol / 2 h / 90 °C

14.1: NMO; OsO₄; H₂O / acetone / 8 h / 25 °C

15.1: 93 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 - 25 °C

16.1: 83 percent / PhSH; BF₃*OEt₂ / CH₂Cl₂ / 2 h / -30 °C

17.1: 98 percent / NEt₃; 4-DMAP / CH₂Cl₂ / 1 h / 0 - 25 °C

With 1,4-diaza-bicyclo[2.2.2]octane; 2,6-dimethylpyridine; dmap; sodium chlorite; sodium dihydrogenphosphate; osmium(VIII) oxide; dipyridinium dichromate; n-butyllithium; sulfuryl dichloride; N-methyl-2-indolinone; 2-methyl-but-2-ene; 3 A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; water; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; thiophenol; triethylamine; N-ethyl-N,N-diisopropylamine; fluoro-N,N,N',N'-tetramethylformamidinium hexafluorophosphate; silver(l) oxide; Wilkinson's catalyst; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; dimethyl sulfoxide; acetone; tert-butyl alcohol; 1.1: Oxidation / 2.1: Methylation / 3.1: Chlorination / 4.1: Etherification / 5.1: Methylation / 6.1: Desilylation / 7.1: Etherification / 8.1: Reduction / 9.1: Oxidation / 10.1: Oxidation / 11.1: Substitution / 12.1: Metallation / 12.2: Esterification / 13.1: Isomerization / 14.1: Oxidation / 15.1: Etherification / 16.1: Dealkylation / 17.1: Acetylation;

DOI:10.1002/(SICI)1521-3773(19991115)38:22<3334::AID-ANIE3334>3.0.CO;2-H

upstream raw materials:

acetic anhydride

triisopropylsilyl trifluoromethanesulfonate

4-Benzyloxy-3,5-dichloro-2-methoxy-6-methyl-benzoic acid (2R,3R,4R,6S)-6-[(2R,3R,4S,5R,6R)-4-benzyloxy-5,6-bis-(4-methoxy-benzyloxy)-2-methyl-tetrahydro-pyran-3-yloxy]-2-methyl-4-triisopropylsilanyloxy-tetrahydro-pyran-3-yl ester

orcinol

Downstream raw materials:

4-benzyloxy-3,5-dichloro-2-methoxy-6-methyl-benzoic acid 6-(5-acetoxy-4-benzyloxy-2-methyl-6-phenylselanyl-tetrahydro-pyran-3-yloxy)-4-(5-methoxy-4,6-dimethyl-4-nitro-tetrahydro-pyran-2-yloxy)-2-methyl-tetrahydro-pyran-3-yl ester

4-benzyloxy-3,5-dichloro-2-methoxy-6-methyl-benzoic acid 6-(4-benzyloxy-6-fluoro-2-methyl-5-phenylselanyl-tetrahydro-pyran-3-yloxy)-4-(5-methoxy-4,6-dimethyl-4-nitro-tetrahydro-pyran-2-yloxy)-2-methyl-tetrahydro-pyran-3-yl ester

4-benzyloxy-3,5-dichloro-2-methoxy-6-methyl-benzoic acid 6-(4-benzyloxy-5-hydroxy-2-methyl-6-phenylselanyl-tetrahydro-pyran-3-yloxy)-4-(5-methoxy-4,6-dimethyl-4-nitro-tetrahydro-pyran-2-yloxy)-2-methyl-tetrahydro-pyran-3-yl ester

4-Benzyloxy-3,5-dichloro-2-methoxy-6-methyl-benzoic acid (2R,3R,4R,6S)-6-[(2R,3R,4S,5R)-5-acetoxy-4-benzyloxy-2-methyl-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yloxy]-2-methyl-4-triisopropylsilanyloxy-tetrahydro-pyran-3-yl ester

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