6-O-benzyl-10-O-t-butyldimethylsilyl catalposide, α ethyl acetal

Base Information

• Chemical Name: 6-O-benzyl-10-O-t-butyldimethylsilyl catalposide, α ethyl acetal
• CAS No.: 109669-25-2
• Molecular Formula: C₃₁H₄₀O₇Si
• Molecular Weight: 552.74
• Mol file: 109669-25-2.mol

Synonyms:

Chemical Property of 6-O-benzyl-10-O-t-butyldimethylsilyl catalposide, α ethyl acetal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-O-benzyl-10-O-t-butyldimethylsilyl catalposide, α ethyl acetal

There total 34 articles about 6-O-benzyl-10-O-t-butyldimethylsilyl catalposide, α ethyl acetal 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: 61.0%

p-(benzyloxy)benzoic acid (1486-51-7) + 10-O-t-butyldimethylsilyl catalpol, α-ethyl acetal (109669-24-1,109717-94-4,121784-80-3) → 6-O-benzyl-10-O-t-butyldimethylsilyl catalposide, α ethyl acetal (109669-25-2,121839-31-4)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide;

DOI:10.1021/ja00251a044

Reference yield:

(2S-cis)-2-ethoxy-3,6-dihydro-2H-pyran-3-acetic acid, methyl ester (109669-17-2) → 6-O-benzyl-10-O-t-butyldimethylsilyl catalposide, α ethyl acetal (109669-25-2,121839-31-4)

Guidance literature:

Multi-step reaction with 11 steps

1: 81 percent / LDA

2: 85 percent / LDA

3: 1.) p-ClC₆H₄NCO, Et₃N, 2.) m-CPBA / 1.) 110 deg C, 3.) benzene, 80 deg C

4: 42 percent / (i-Bu)2nBuAlH, Li⁽¹⁺⁾

5: 72 percent / DMAP, Et₃N

6: 77 percent / 3,5-DNPBA, Na₂HPO₄ / CH₂Cl₂

7: 57 percent / H₂, B(OH)3 / Rh-Al / methanol; H₂O

8: 70 percent / CH₃SO₂Cl, Et₃N

9: 93 percent / LAH / tetrahydrofuran / -78 °C

10: 64 percent / RuH₂(PPh₃)4 / ethanol

11: 61 percent / DCC, DMAP

With dmap; disodium hydrogenphosphate; lithium aluminium tetrahydride; n-butyl-diisobutylaluminum hydride; 3,5-dinitrobenzoperoxoic acid; lithium cation; hydrogen; boric acid; p-chlorphenylisocyanate; methanesulfonyl chloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; lithium diisopropyl amide; dihydridotetrakis(triphenylphosphine)ruthenium; rhodium on aluminium; In tetrahydrofuran; methanol; ethanol; dichloromethane; water;

DOI:10.1021/ja00251a044

Reference yield:

<2S-<2α,3α(R*)>>-2-ethoxy-3,6-dihydro-3-(1'-thiophenyl)-2H-pyran-3-acetic acid, methyl ester (109686-28-4,121681-23-0,121681-24-1,121681-27-4,121703-61-5) → 6-O-benzyl-10-O-t-butyldimethylsilyl catalposide, α ethyl acetal (109669-25-2,121839-31-4)

Guidance literature:

Multi-step reaction with 10 steps

1: 85 percent / LDA

2: 1.) p-ClC₆H₄NCO, Et₃N, 2.) m-CPBA / 1.) 110 deg C, 3.) benzene, 80 deg C

3: 42 percent / (i-Bu)2nBuAlH, Li⁽¹⁺⁾

4: 72 percent / DMAP, Et₃N

5: 77 percent / 3,5-DNPBA, Na₂HPO₄ / CH₂Cl₂

6: 57 percent / H₂, B(OH)3 / Rh-Al / methanol; H₂O

7: 70 percent / CH₃SO₂Cl, Et₃N

8: 93 percent / LAH / tetrahydrofuran / -78 °C

9: 64 percent / RuH₂(PPh₃)4 / ethanol

10: 61 percent / DCC, DMAP

With dmap; disodium hydrogenphosphate; lithium aluminium tetrahydride; n-butyl-diisobutylaluminum hydride; 3,5-dinitrobenzoperoxoic acid; lithium cation; hydrogen; boric acid; p-chlorphenylisocyanate; methanesulfonyl chloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; lithium diisopropyl amide; dihydridotetrakis(triphenylphosphine)ruthenium; rhodium on aluminium; In tetrahydrofuran; methanol; ethanol; dichloromethane; water;

DOI:10.1021/ja00251a044

upstream raw materials:

p-(benzyloxy)benzoic acid

10-O-t-butyldimethylsilyl catalpol, β-ethyl acetal

10-O-t-butyldimethylsilyl catalpol, α-ethyl acetal

(2S-cis)-2-ethoxy-3,6-dihydro-2H-pyran-3-acetic acid, methyl ester

Downstream raw materials:

4-Benzyloxy-benzoic acid (1aS,1bS,2R,5aR,6S,6aS)-1a-(tert-butyl-dimethyl-silanyloxymethyl)-2,4-diethoxy-octahydro-1,3-dioxa-cyclopropa[a]inden-6-yl ester

1β,3α-specionin

(-)-specionin

1β,3β-specionin