ethyl 2-<(1S,5S,6S)-5,6-di-(4-methoxybenzyl)oxy-cyclohex-2-en-1-yl>propionate

Base Information

• Chemical Name: ethyl 2-<(1S,5S,6S)-5,6-di-(4-methoxybenzyl)oxy-cyclohex-2-en-1-yl>propionate
• CAS No.: 210764-98-0
• Molecular Formula: C₂₇H₃₄O₆
• Molecular Weight: 454.563
• Mol file: 210764-98-0.mol

Synonyms:ethyl 2-<(1S,5S,6S)-5,6-di-(4-methoxybenzyl)oxy-cyclohex-2-en-1-yl>propionate

Chemical Property of ethyl 2-<(1S,5S,6S)-5,6-di-(4-methoxybenzyl)oxy-cyclohex-2-en-1-yl>propionate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 2-<(1S,5S,6S)-5,6-di-(4-methoxybenzyl)oxy-cyclohex-2-en-1-yl>propionate

There total 13 articles about ethyl 2-<(1S,5S,6S)-5,6-di-(4-methoxybenzyl)oxy-cyclohex-2-en-1-yl>propionate 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: 74.0%

(1R,4S,5S)-4,5-di-(4-methoxybenzyl)oxy-cyclohex-2-en-1-ol (210764-97-9) + Triethyl orthopropionate (115-80-0) → ethyl 2-<(1S,5S,6S)-5,6-di-(4-methoxybenzyl)oxy-cyclohex-2-en-1-yl>propionate (210764-98-0)

Guidance literature:

With propionic acid; at 140 ℃;

DOI:10.1039/a802169d

Reference yield:

(4S,5R,6S)-6-acetoxy-4,5-di-(4-methoxybenzyl)oxy-cyclohex-2-en-1-one (210764-93-5) → ethyl 2-<(1S,5S,6S)-5,6-di-(4-methoxybenzyl)oxy-cyclohex-2-en-1-yl>propionate (210764-98-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 90 percent / CeCl₃*7H₂O, NaBH₄ / methanol / 0.25 h / 0 °C

2: 90 percent / PPTS / CH₂Cl₂ / 24 h / Ambient temperature

3: 87 percent / NaOMe / methanol / 15 h / Ambient temperature

4: 1.) NaH, imidazole / 1.) THF, 0 deg C, 40 min, 2.) 0 deg C, 1.5 h, 3.) 0 deg C, 30 min

5: 71 percent / AIBN, n-Bu₃SnH / toluene / 15 h / Heating

6: 96 percent / PPTS / ethanol / 3 h / 50 °C

7: 74 percent / propionic acid / 2 h / 140 °C

With 1H-imidazole; sodium tetrahydroborate; cerium(III) chloride; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium methylate; pyridinium p-toluenesulfonate; sodium hydride; propionic acid; In methanol; ethanol; dichloromethane; toluene;

DOI:10.1016/S0040-4020(99)00004-6

Reference yield:

methyl 4-O-acetyl-2,3-di-O-(4-methoxy)benzyl-α-D-xylo-hex-5-enopyranoside (210764-92-4) → ethyl 2-<(1S,5S,6S)-5,6-di-(4-methoxybenzyl)oxy-cyclohex-2-en-1-yl>propionate (210764-98-0)

Guidance literature:

Multi-step reaction with 9 steps

1: 100 percent / Hg(OCOCF₃)2 / acetone; H₂O / 15 h / Ambient temperature

2: 84 percent / MsCl / CH₂Cl₂ / 2 h / 0 °C

3: 90 percent / CeCl₃*7H₂O, NaBH₄ / methanol / 0.25 h / 0 °C

4: 90 percent / PPTS / CH₂Cl₂ / 24 h / Ambient temperature

5: 87 percent / NaOMe / methanol / 15 h / Ambient temperature

6: 1.) NaH, imidazole / 1.) THF, 0 deg C, 40 min, 2.) 0 deg C, 1.5 h, 3.) 0 deg C, 30 min

7: 71 percent / AIBN, n-Bu₃SnH / toluene / 15 h / Heating

8: 96 percent / PPTS / ethanol / 3 h / 50 °C

9: 74 percent / propionic acid / 2 h / 140 °C

With 1H-imidazole; sodium tetrahydroborate; cerium(III) chloride; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium methylate; mercury(II) trifluoroacetate; pyridinium p-toluenesulfonate; sodium hydride; propionic acid; methanesulfonyl chloride; In methanol; ethanol; dichloromethane; water; acetone; toluene;

DOI:10.1016/S0040-4020(99)00004-6

upstream raw materials:

(1R,4S,5S)-4,5-di-(4-methoxybenzyl)oxy-cyclohex-2-en-1-ol

Triethyl orthopropionate

p-methoxybenzyl chloride

methyl 2,3-di-O-(4-methoxyphenylmethyl)-α-D-glucopyranoside

Downstream raw materials:

(1R,2R,3S,4S)-2-<(1R)-1-methylprop-2-en-1-yl>-3,4-di-(4-methoxybenzyl)oxy-cyclohexan-1-ol

(3S,3aR,4S,5S,7aR)-4,5-Bis-(4-methoxy-benzyloxy)-3-methyl-octahydro-benzofuran-2-ol

(3S,3aS,4S,5S,7aR)-4,5-di-(4-methoxybenzyl)oxy-3-methyl-3a,4,5,6,7,7a-hexahydrobenzofuran-2(3H)-one

(1R,2R,3S,4S)-2-<(1E)-3-hydroxy-1-methylprop-1-en-1-yl>-3,4-di-(4-methoxybenzyl)oxy-cyclohexan-1-ol

Refernces

• 1、 Amano, Seiji,Ogawa, Noriko,Ohtsuka, Masami,Ogawa, Seiichiro,Chida, Noritaka. "Total synthesis and absolute configuration of FR65814". . p. 1263 - 1264. Retrieved 2007/10/03.