10-(t-butyldimethylsilyloxy)-5,7-dimethoxy-1-(ethoxycarbonylmethyl)-2-[tris(1-methylethyl)silyloxy]-6H-furo[2,3-c]-xanthene-Δ^9,δ-butane

Base Information

• Chemical Name: 10-(t-butyldimethylsilyloxy)-5,7-dimethoxy-1-(ethoxycarbonylmethyl)-2-[tris(1-methylethyl)silyloxy]-6H-furo[2,3-c]-xanthene-Δ^9,δ-butane
• CAS No.: 438497-22-4
• Molecular Formula: C₄₀H₆₂O₈Si₂
• Molecular Weight: 727.098
• Mol file: 438497-22-4.mol

Synonyms:10-(t-butyldimethylsilyloxy)-5,7-dimethoxy-1-(ethoxycarbonylmethyl)-2-[tris(1-methylethyl)silyloxy]-6H-furo[2,3-c]-xanthene-Δ^9,δ-butane

Chemical Property of 10-(t-butyldimethylsilyloxy)-5,7-dimethoxy-1-(ethoxycarbonylmethyl)-2-[tris(1-methylethyl)silyloxy]-6H-furo[2,3-c]-xanthene-Δ^9,δ-butane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 10-(t-butyldimethylsilyloxy)-5,7-dimethoxy-1-(ethoxycarbonylmethyl)-2-[tris(1-methylethyl)silyloxy]-6H-furo[2,3-c]-xanthene-Δ^9,δ-butane

There total 1 articles about 10-(t-butyldimethylsilyloxy)-5,7-dimethoxy-1-(ethoxycarbonylmethyl)-2-[tris(1-methylethyl)silyloxy]-6H-furo[2,3-c]-xanthene-Δ^9,δ-butane 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%

triisopropylsilyl trifluoromethanesulfonate (80522-42-5) + 5-(t-butyldimethylsilyloxy)-1,8-dimethoxy-4-(ethyl-3'-formylpropanoate)-3-O-methoxymethyl-9H-xanthen-Δ9,δ-butane (438497-21-3) → 10-(t-butyldimethylsilyloxy)-5,7-dimethoxy-1-(ethoxycarbonylmethyl)-2-[tris(1-methylethyl)silyloxy]-6H-furo[2,3-c]-xanthene-Δ9,δ-butane (438497-22-4)

Guidance literature:

In tetrahydrofuran; at 0 ℃; for 3h;

DOI:10.1021/ja012185v

Reference yield:

10-(t-butyldimethylsilyloxy)-5,7-dimethoxy-1-(ethoxycarbonylmethyl)-2-[tris(1-methylethyl)silyloxy]-6H-furo[2,3-c]-xanthene-Δ9,δ-butane (438497-22-4) → endo-6,8-dimethoxy-11-hydroxy-2-thiophenyl-7H-1,2-dihydrofuro[2','3:4,5]furo[2,3-c]-xanthen-7-one

Guidance literature:

Multi-step reaction with 4 steps

1: DIBAL / CH₂Cl₂ / 0.5 h / -78 °C

2: 88 percent / m-CPBA; 4A molecular sieves / CH₂Cl₂ / 0.17 h

3: 73 percent / TEA*(HF)3 / acetonitrile / 1 h

4: 4A molecular sieves; Amberlyst 15 resin / acetonitrile / 2 h / Heating

With Amberlyst 15 resin; 4 A molecular sieve; diisobutylaluminium hydride; triethylamine tris(hydrogen fluoride); 3-chloro-benzenecarboperoxoic acid; In dichloromethane; acetonitrile;

DOI:10.1021/ja012185v

Reference yield:

10-(t-butyldimethylsilyloxy)-5,7-dimethoxy-1-(ethoxycarbonylmethyl)-2-[tris(1-methylethyl)silyloxy]-6H-furo[2,3-c]-xanthene-Δ9,δ-butane (438497-22-4) → exo-6,8-dimethoxy-11-hydroxy-2-thiophenyl-7H-1,2-dihydrofuro[2','3:4,5]furo[2,3-c]-xanthen-7-one

Guidance literature:

Multi-step reaction with 4 steps

1: DIBAL / CH₂Cl₂ / 0.5 h / -78 °C

2: 88 percent / m-CPBA; 4A molecular sieves / CH₂Cl₂ / 0.17 h

3: 73 percent / TEA*(HF)3 / acetonitrile / 1 h

4: 4A molecular sieves; Amberlyst 15 resin / acetonitrile / 2 h / Heating

With Amberlyst 15 resin; 4 A molecular sieve; diisobutylaluminium hydride; triethylamine tris(hydrogen fluoride); 3-chloro-benzenecarboperoxoic acid; In dichloromethane; acetonitrile;

DOI:10.1021/ja012185v

upstream raw materials:

triisopropylsilyl trifluoromethanesulfonate

5-(t-butyldimethylsilyloxy)-1,8-dimethoxy-4-(ethyl-3'-formylpropanoate)-3-O-methoxymethyl-9H-xanthen-Δ^9,δ-butane