(2R,4aR,6S,7S,8S,8aR)-7-(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]-8-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

Base Information

• Chemical Name: (2R,4aR,6S,7S,8S,8aR)-7-(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]-8-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol
• CAS No.: 256413-38-4
• Molecular Formula: C₄₂H₇₈O₁₀Si₃
• Molecular Weight: 827.332
• Mol file: 256413-38-4.mol

Synonyms:(2R,4aR,6S,7S,8S,8aR)-7-(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]-8-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

Chemical Property of (2R,4aR,6S,7S,8S,8aR)-7-(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]-8-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4aR,6S,7S,8S,8aR)-7-(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]-8-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

There total 19 articles about (2R,4aR,6S,7S,8S,8aR)-7-(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]-8-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol 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:

phenyl 4,6-di-O-benzylidene-1-thio-β-D-galactopyranoside (71676-30-7,87508-17-6,138922-03-9,87508-18-7) → (2R,4aR,6S,7S,8S,8aR)-7-(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]-8-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol (256413-38-4)

Guidance literature:

Multi-step reaction with 13 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

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; zinc trifluoromethanesulfonate; sodium hydride; di(n-butyl)tin oxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; ethanethiol; In tetrahydrofuran; diethyl ether; dichloromethane; 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;

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

Reference yield:

phenyl 4,6-O-benzylidene-3-O-(4-methoxybenzyl)-1-thio-α-D-mannopyranoside (168138-26-9) → (2R,4aR,6S,7S,8S,8aR)-7-(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]-8-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol (256413-38-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 93 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 - 25 °C

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

3: 71 percent / Tf₂O; di-tert-butyl-4-methylpyridine; molecular sieves 4 Angstroem / CH₂Cl₂ / 2.5 h / -78 - 0 °C

4: 95 percent / DDQ; H₂O / CH₂Cl₂ / 2 h / 0 - 25 °C

5: 0.46 g / NMO; TPAP; molecular sieves 4 Angstroem / CH₂Cl₂ / 2 h / 25 °C

6: 0.44 g / diethyl ether / 1 h / -78 °C

With 2,6-dimethylpyridine; N-methyl-2-indolinone; tetrapropylammonium perruthennate; di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride; 4 A molecular sieve; water; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In diethyl ether; dichloromethane; 1: Etherification / 2: Oxidation / 3: Glycosidation / 4: Oxidation / 5: Oxidation / 6: Methylation;

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

Reference yield:

phenyl 4,6-O-benzylidene-3-O-(p-methoxybenzyl)-1-thio-β-D-galactopyranoside (179072-68-5) → (2R,4aR,6S,7S,8S,8aR)-7-(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]-8-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol (256413-38-4)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 - 25 °C

2.1: 77 percent / EtSH; Zn(OTf)2 / CH₂Cl₂ / 2 h / 0 °C

3.1: 97 percent / pyridine / 12 h / 0 - 25 °C

4.1: 90 percent / LAH / tetrahydrofuran / 3 h / 0 - 45 °C

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

5.2: 94 percent / dimethylformamide / 1 h / 0 - 25 °C

6.1: 95 percent / NBS; H₂O / acetone / 2 h / 0 - 25 °C

7.1: 2,6-lutidine / CH₂Cl₂ / 6 h / 0 - 25 °C

8.1: 98 percent / DDQ; H₂O / CH₂Cl₂ / 1 h / 0 - 25 °C

9.1: 71 percent / Tf₂O; di-tert-butyl-4-methylpyridine; molecular sieves 4 Angstroem / CH₂Cl₂ / 2.5 h / -78 - 0 °C

10.1: 95 percent / DDQ; H₂O / CH₂Cl₂ / 2 h / 0 - 25 °C

11.1: 0.46 g / NMO; TPAP; molecular sieves 4 Angstroem / CH₂Cl₂ / 2 h / 25 °C

12.1: 0.44 g / diethyl ether / 1 h / -78 °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; zinc trifluoromethanesulfonate; sodium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; ethanethiol; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetone; 1.1: Etherification / 2.1: Ring cleavage / 3.1: Tosylation / 4.1: Reduction / 5.1: Metallation / 5.2: Methylation / 6.1: Hydrolysis / 7.1: Etherification / 8.1: Hydrolysis / 9.1: Glycosidation / 10.1: Oxidation / 11.1: Oxidation / 12.1: Methylation;

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

upstream raw materials:

methyllithium

(2R,4aR,6S,7R,8aR)-7-(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-phenyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-one

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

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