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
Hs Code.:

Synonyms:

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

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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%

: 1486-51-7
p-(benzyloxy)benzoic acid

: 109669-24-1,109717-94-4,121784-80-3
10-O-t-butyldimethylsilyl catalpol, α-ethyl acetal

: 109669-25-2,121839-31-4
6-O-benzyl-10-O-t-butyldimethylsilyl catalposide, α ethyl acetal

Guidance literature:: With dmap; dicyclohexyl-carbodiimide;
DOI:10.1021/ja00251a044

Reference yield:

: 109669-17-2
(2S-cis)-2-ethoxy-3,6-dihydro-2H-pyran-3-acetic acid, methyl ester

: 109669-25-2,121839-31-4
6-O-benzyl-10-O-t-butyldimethylsilyl catalposide, α ethyl acetal

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:

: 109686-28-4,121681-23-0,121681-24-1,121681-27-4,121703-61-5
<2S-<2α,3α(R^*)>>-2-ethoxy-3,6-dihydro-3-(1'-thiophenyl)-2H-pyran-3-acetic acid, methyl ester

: 109669-25-2,121839-31-4
6-O-benzyl-10-O-t-butyldimethylsilyl catalposide, α ethyl acetal

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