[3S-[3*R[E(1S*,3S*4S*)],4S*,5R*,8S*,9E,12R*,14R*,15S*,16R*,18S*,19S*,26aR*]]-3-[2-[4-[4-(3,5-Dimethoxyphenyl)-1H-imidazol-2-ylmethoxy]-3-methoxycyclohexyl]-1-methylethenyl]-8-ethyl-5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-5,19-dihydroxy

Base Information

• Chemical Name: [3S-[3*R[E(1S*,3S*4S*)],4S*,5R*,8S*,9E,12R*,14R*,15S*,16R*,18S*,19S*,26aR*]]-3-[2-[4-[4-(3,5-Dimethoxyphenyl)-1H-imidazol-2-ylmethoxy]-3-methoxycyclohexyl]-1-methylethenyl]-8-ethyl-5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-5,19-dihydroxy
• CAS No.: 150250-95-6
• Molecular Formula: C₅₅H₈₁N₃O₁₄
• Molecular Weight: 1008.26
• Mol file: 150250-95-6.mol

Synonyms:15,19-Epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclotricosine-1,7,20,21(4H,23H)-tetrone,3-[2-[4-[[4-(3,5-dimethoxyphenyl)-1H-imidazol-2-yl]methoxy]-3-methoxycyclohexyl]-1-methylethenyl]-8-ethyl-5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-5,19-dihydroxy-14,16-dimethoxy-4,10,12,18-tetramethyl-,[3S-[3R*[E(1S*,3S*,4S*)],4S*,5R*,8S*,9E,12R*,14R*,15S*,16R*,18S*,19S*,26aR*]]-;L 733725

Chemical Property of [3S-[3*R[E(1S*,3S*4S*)],4S*,5R*,8S*,9E,12R*,14R*,15S*,16R*,18S*,19S*,26aR*]]-3-[2-[4-[4-(3,5-Dimethoxyphenyl)-1H-imidazol-2-ylmethoxy]-3-methoxycyclohexyl]-1-methylethenyl]-8-ethyl-5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-5,19-dihydroxy

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [3S-[3*R[E(1S*,3S*4S*)],4S*,5R*,8S*,9E,12R*,14R*,15S*,16R*,18S*,19S*,26aR*]]-3-[2-[4-[4-(3,5-Dimethoxyphenyl)-1H-imidazol-2-ylmethoxy]-3-methoxycyclohexyl]-1-methylethenyl]-8-ethyl-5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-5,19-dihydroxy

There total 8 articles about [3S-[3*R[E(1S*,3S*4S*)],4S*,5R*,8S*,9E,12R*,14R*,15S*,16R*,18S*,19S*,26aR*]]-3-[2-[4-[4-(3,5-Dimethoxyphenyl)-1H-imidazol-2-ylmethoxy]-3-methoxycyclohexyl]-1-methylethenyl]-8-ethyl-5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-5,19-dihydroxy 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:

1-(3,5-dimethoxyphenyl)ethan-1-one (39151-19-4) → L-733,725 (150250-95-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 77 percent / aq. HBr / dimethylsulfoxide / 8 h / 60 - 68 °C

2: 63 percent / NH₄OAc / acetonitrile / 2 h / 0 °C

3: 82 percent / p-TsOH*H₂O / tetrahydrofuran / 2 h / 50 °C

4: LiBH₄ / methanol; tetrahydrofuran / 2 h / 10 - 15 °C

5: 87 percent / K₂CO₃, DBU / ethyl acetate

6: 1.) TfOH, t-BuCONHMe₂, 2.) TfOH / 1.) MeCN, -33 to 0 deg C, 2.) MeCN, H₂O, 50 deg C, overnight

With lithium borohydride; trifluorormethanesulfonic acid; t-BuCONHMe₂; ammonium acetate; hydrogen bromide; potassium carbonate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; methanol; dimethyl sulfoxide; ethyl acetate; acetonitrile;

DOI:10.1021/jo981805g

Reference yield:

3',5'-dimethoxyphenylglyoxal monohydrate (188199-78-2) → L-733,725 (150250-95-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 63 percent / NH₄OAc / acetonitrile / 2 h / 0 °C

2: 82 percent / p-TsOH*H₂O / tetrahydrofuran / 2 h / 50 °C

3: LiBH₄ / methanol; tetrahydrofuran / 2 h / 10 - 15 °C

4: 87 percent / K₂CO₃, DBU / ethyl acetate

5: 1.) TfOH, t-BuCONHMe₂, 2.) TfOH / 1.) MeCN, -33 to 0 deg C, 2.) MeCN, H₂O, 50 deg C, overnight

With lithium borohydride; trifluorormethanesulfonic acid; t-BuCONHMe₂; ammonium acetate; potassium carbonate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; methanol; ethyl acetate; acetonitrile;

DOI:10.1021/jo981805g

Reference yield:

2-carbomethoxy-4(5)-(3',5'-dimethoxyphenyl)imidazole (188199-81-7) → L-733,725 (150250-95-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 82 percent / p-TsOH*H₂O / tetrahydrofuran / 2 h / 50 °C

2: LiBH₄ / methanol; tetrahydrofuran / 2 h / 10 - 15 °C

3: 87 percent / K₂CO₃, DBU / ethyl acetate

4: 1.) TfOH, t-BuCONHMe₂, 2.) TfOH / 1.) MeCN, -33 to 0 deg C, 2.) MeCN, H₂O, 50 deg C, overnight

With lithium borohydride; trifluorormethanesulfonic acid; t-BuCONHMe₂; potassium carbonate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; methanol; ethyl acetate;

DOI:10.1021/jo981805g

upstream raw materials:

3,5-dimethoxyphenylglyoxal

ascomycin

1-(2'-tetrahydrofuranyl)-2-trichloroacetimidoxymethyl-4⁽⁵⁾-(3'',5''-dimethoxyphenyl)imidazole

1-(3,5-dimethoxyphenyl)ethan-1-one