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

Base Information

• Chemical Name: 4-Benzyloxy-benzoic acid (1aS,1bS,2S,4S,5aR,6S,6aS)-1a-(tert-butyl-dimethyl-silanyloxymethyl)-2,4-diethoxy-octahydro-1,3-dioxa-cyclopropa[a]inden-6-yl ester
• CAS No.: 109519-11-1
• Molecular Formula: C₃₃H₄₆O₈Si
• Molecular Weight: 598.809
• Mol file: 109519-11-1.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 51 articles about 4-Benzyloxy-benzoic acid (1aS,1bS,2S,4S,5aR,6S,6aS)-1a-(tert-butyl-dimethyl-silanyloxymethyl)-2,4-diethoxy-octahydro-1,3-dioxa-cyclopropa[a]inden-6-yl ester 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: 70.0%

ethanol (64-17-5) + 6-O-benzyl-10-O-t-butyldimethylsilyl catalposide, α ethyl acetal (109669-25-2,121839-31-4) → 6-O-benzyl-10-O-t-butyldimethylsilyl specionin (109519-11-1,109784-38-5,121784-81-4,121784-82-5)

Guidance literature:

With sodium hydroxide; sodium tetrahydroborate; mercury(II) diacetate;

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 specionin (109519-11-1,109784-38-5,121784-81-4,121784-82-5)

Guidance literature:

Multi-step reaction with 12 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

12: 70 percent / 1.) Hg(OAc)2, 2.) NaBH₄, NaOH

With dmap; sodium hydroxide; sodium tetrahydroborate; disodium hydrogenphosphate; lithium aluminium tetrahydride; n-butyl-diisobutylaluminum hydride; 3,5-dinitrobenzoperoxoic acid; mercury(II) diacetate; 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 specionin (109519-11-1,109784-38-5,121784-81-4,121784-82-5)

Guidance literature:

Multi-step reaction with 11 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

11: 70 percent / 1.) Hg(OAc)2, 2.) NaBH₄, NaOH

With dmap; sodium hydroxide; sodium tetrahydroborate; disodium hydrogenphosphate; lithium aluminium tetrahydride; n-butyl-diisobutylaluminum hydride; 3,5-dinitrobenzoperoxoic acid; mercury(II) diacetate; 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:

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

Ethyl-2,3-dideoxy-4-O-acetyl-D-glycero-pent-2-enopyranosid

p-(benzyloxy)benzoic acid

tert-butyldimethylsilyl chloride

Downstream raw materials:

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

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

1β,3α-specionin

(-)-specionin