toluene-4-sulfonic acid 5-(tert-butyl-dimethyl-silanyloxy)-6-[3-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methyl-2-triisopropylsilanyloxy-tetrahydro-pyran-4-yloxy]-3,4-dihydroxy-4-methyl-tetrahydro-pyran-2-ylmethyl ester

Base Information

• Chemical Name: toluene-4-sulfonic acid 5-(tert-butyl-dimethyl-silanyloxy)-6-[3-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methyl-2-triisopropylsilanyloxy-tetrahydro-pyran-4-yloxy]-3,4-dihydroxy-4-methyl-tetrahydro-pyran-2-ylmethyl ester
• CAS No.: 256413-39-5
• Molecular Formula: C₄₂H₈₀O₁₂SSi₃
• Molecular Weight: 893.412
• Mol file: 256413-39-5.mol

Synonyms:toluene-4-sulfonic acid 5-(tert-butyl-dimethyl-silanyloxy)-6-[3-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methyl-2-triisopropylsilanyloxy-tetrahydro-pyran-4-yloxy]-3,4-dihydroxy-4-methyl-tetrahydro-pyran-2-ylmethyl ester

Chemical Property of toluene-4-sulfonic acid 5-(tert-butyl-dimethyl-silanyloxy)-6-[3-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methyl-2-triisopropylsilanyloxy-tetrahydro-pyran-4-yloxy]-3,4-dihydroxy-4-methyl-tetrahydro-pyran-2-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of toluene-4-sulfonic acid 5-(tert-butyl-dimethyl-silanyloxy)-6-[3-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methyl-2-triisopropylsilanyloxy-tetrahydro-pyran-4-yloxy]-3,4-dihydroxy-4-methyl-tetrahydro-pyran-2-ylmethyl ester

There total 21 articles about toluene-4-sulfonic acid 5-(tert-butyl-dimethyl-silanyloxy)-6-[3-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methyl-2-triisopropylsilanyloxy-tetrahydro-pyran-4-yloxy]-3,4-dihydroxy-4-methyl-tetrahydro-pyran-2-ylmethyl 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: 87.0%

p-toluenesulfonyl chloride (98-59-9) + (2R,3R,4S,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-[(2S,3R,4S,5S,6R)-3-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methyl-2-triisopropylsilanyloxy-tetrahydro-pyran-4-yloxy]-2-hydroxymethyl-4-methyl-tetrahydro-pyran-3,4-diol (256413-58-8) → toluene-4-sulfonic acid 5-(tert-butyl-dimethyl-silanyloxy)-6-[3-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methyl-2-triisopropylsilanyloxy-tetrahydro-pyran-4-yloxy]-3,4-dihydroxy-4-methyl-tetrahydro-pyran-2-ylmethyl ester (256413-39-5)

Guidance literature:

With pyridine; at 0 - 25 ℃; for 12h;

DOI:10.1002/(SICI)1521-3773(19991115)38:22<3345::AID-ANIE3345>3.0.CO;2-9 DOI:10.1002/1521-3765(20000901)6:17<3149::AID-CHEM3149>3.0.CO;2-L

Reference yield:

phenyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside (159407-19-9) → toluene-4-sulfonic acid 5-(tert-butyl-dimethyl-silanyloxy)-6-[3-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methyl-2-triisopropylsilanyloxy-tetrahydro-pyran-4-yloxy]-3,4-dihydroxy-4-methyl-tetrahydro-pyran-2-ylmethyl ester (256413-39-5)

Guidance literature:

Multi-step reaction with 9 steps

1.1: nBu₂SnO / toluene / 3 h / Heating

1.2: 83 percent / nBu₄NI / 2 h / 25 - 110 °C

2.1: 93 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 - 25 °C

3.1: 92 percent / mCPBA / CH₂Cl₂ / 2 h / -20 - 0 °C

4.1: 71 percent / Tf₂O; di-tert-butyl-4-methylpyridine; molecular sieves 4 Angstroem / CH₂Cl₂ / 2.5 h / -78 - 0 °C

5.1: 95 percent / DDQ; H₂O / CH₂Cl₂ / 2 h / 0 - 25 °C

6.1: 0.46 g / NMO; TPAP; molecular sieves 4 Angstroem / CH₂Cl₂ / 2 h / 25 °C

7.1: 0.44 g / diethyl ether / 1 h / -78 °C

8.1: 97 percent / H₂ / 10 percent Pd/C / ethyl acetate / 2 h / 25 °C

9.1: 87 percent / pyridine / 12 h / 0 - 25 °C

With pyridine; 2,6-dimethylpyridine; N-methyl-2-indolinone; tetrapropylammonium perruthennate; di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride; 4 A molecular sieve; water; hydrogen; di(n-butyl)tin oxide; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium on activated charcoal; In diethyl ether; dichloromethane; ethyl acetate; toluene; 1.1: Cyclization / 1.2: Ring cleavage / 2.1: Etherification / 3.1: Oxidation / 4.1: Glycosidation / 5.1: Oxidation / 6.1: Oxidation / 7.1: Methylation / 8.1: Hydrogenolysis / 9.1: Tosylation;

DOI:10.1002/1521-3765(20000901)6:17<3149::AID-CHEM3149>3.0.CO;2-L

Reference yield:

phenyl 4,6-di-O-benzylidene-1-thio-β-D-galactopyranoside (71676-30-7,87508-17-6,138922-03-9,87508-18-7) → toluene-4-sulfonic acid 5-(tert-butyl-dimethyl-silanyloxy)-6-[3-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methyl-2-triisopropylsilanyloxy-tetrahydro-pyran-4-yloxy]-3,4-dihydroxy-4-methyl-tetrahydro-pyran-2-ylmethyl ester (256413-39-5)

Guidance literature:

Multi-step reaction with 15 steps

1.1: nBu₂SnO / toluene / 3 h / Heating

1.2: 87 percent / nBu₄NI / 2 h / 25 - 110 °C

2.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 - 25 °C

3.1: 77 percent / EtSH; Zn(OTf)2 / CH₂Cl₂ / 2 h / 0 °C

4.1: 97 percent / pyridine / 12 h / 0 - 25 °C

5.1: 90 percent / LAH / tetrahydrofuran / 3 h / 0 - 45 °C

6.1: NaH / dimethylformamide / 0.08 h / 0 °C

6.2: 94 percent / dimethylformamide / 1 h / 0 - 25 °C

7.1: 95 percent / NBS; H₂O / acetone / 2 h / 0 - 25 °C

8.1: 2,6-lutidine / CH₂Cl₂ / 6 h / 0 - 25 °C

9.1: 98 percent / DDQ; H₂O / CH₂Cl₂ / 1 h / 0 - 25 °C

10.1: 71 percent / Tf₂O; di-tert-butyl-4-methylpyridine; molecular sieves 4 Angstroem / CH₂Cl₂ / 2.5 h / -78 - 0 °C

11.1: 95 percent / DDQ; H₂O / CH₂Cl₂ / 2 h / 0 - 25 °C

12.1: 0.46 g / NMO; TPAP; molecular sieves 4 Angstroem / CH₂Cl₂ / 2 h / 25 °C

13.1: 0.44 g / diethyl ether / 1 h / -78 °C

14.1: 97 percent / H₂ / 10 percent Pd/C / ethyl acetate / 2 h / 25 °C

15.1: 87 percent / pyridine / 12 h / 0 - 25 °C

With pyridine; 2,6-dimethylpyridine; N-Bromosuccinimide; lithium aluminium tetrahydride; N-methyl-2-indolinone; tetrapropylammonium perruthennate; di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride; 4 A molecular sieve; water; hydrogen; zinc trifluoromethanesulfonate; sodium hydride; di(n-butyl)tin oxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; ethanethiol; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; 1.1: Cyclization / 1.2: Ring cleavage / 2.1: Etherification / 3.1: Ring cleavage / 4.1: Tosylation / 5.1: Reduction / 6.1: Metallation / 6.2: Methylation / 7.1: Hydrolysis / 8.1: Etherification / 9.1: Hydrolysis / 10.1: Glycosidation / 11.1: Oxidation / 12.1: Oxidation / 13.1: Methylation / 14.1: Hydrogenolysis / 15.1: Tosylation;

DOI:10.1002/1521-3765(20000901)6:17<3149::AID-CHEM3149>3.0.CO;2-L

upstream raw materials:

p-toluenesulfonyl chloride

(2R,3R,4S,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-[(2S,3R,4S,5S,6R)-3-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methyl-2-triisopropylsilanyloxy-tetrahydro-pyran-4-yloxy]-2-hydroxymethyl-4-methyl-tetrahydro-pyran-3,4-diol

t-butyldimethylsiyl triflate

phenyl 4,6-di-O-benzylidene-1-thio-β-D-galactopyranoside

Downstream raw materials:

Acetic acid (2S,3S,4S,5R,6R)-2-((3R,4S,5S,6R)-2,3-diacetoxy-5-methoxy-6-methyl-tetrahydro-pyran-4-yloxy)-4-hydroxy-5-(4-methoxy-benzyloxy)-4,6-dimethyl-tetrahydro-pyran-3-yl ester

(2S,3S,4S,5R,6R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(2S,3R,4S,5S,6R)-3-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methyl-2-triisopropylsilanyloxy-tetrahydro-pyran-4-yloxy]-5-(4-methoxy-benzyloxy)-4,6-dimethyl-tetrahydro-pyran-4-ol