(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

Base Information

• Chemical Name: (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
• CAS No.: 306747-66-0
• Molecular Formula: C₄₁H₇₄O₁₀Si₃
• Molecular Weight: 811.289

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (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

There total 18 articles about (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 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,4aR,6S,7S,8S,8aS)-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-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol (256413-37-3) → (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 (306747-66-0)

Guidance literature:

With N-methyl-2-indolinone; tetrapropylammonium perruthennate; In dichloromethane; at 25 ℃; for 2h;

DOI:10.1002/(SICI)1521-3773(19991115)38:22<3345::AID-ANIE3345>3.0.CO;2-9

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,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 (306747-66-0)

Guidance literature:

Multi-step reaction with 12 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

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; 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;

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,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 (306747-66-0)

Guidance literature:

Multi-step reaction with 5 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

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 dichloromethane; 1: Etherification / 2: Oxidation / 3: Glycosidation / 4: Oxidation / 5: Oxidation;

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

upstream raw materials:

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

t-butyldimethylsiyl triflate

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

phenyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside

Downstream raw materials:

(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

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

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