Phosphonic acid, [8-[(3,4-dimethoxyphenyl)methoxy]-2-hydroxy-6-[(4-methoxyphenyl)meth oxy]-3,5,7,9-tetramethyl-10-undecenyl]-, dimethyl ester

Base Information

• Chemical Name: Phosphonic acid, [8-[(3,4-dimethoxyphenyl)methoxy]-2-hydroxy-6-[(4-methoxyphenyl)meth oxy]-3,5,7,9-tetramethyl-10-undecenyl]-, dimethyl ester
• CAS No.: 113956-93-7
• Molecular Formula: C34H53O9P
• Molecular Weight: 636.763
• Mol file: 113956-93-7.mol

Synonyms:

Chemical Property of Phosphonic acid, [8-[(3,4-dimethoxyphenyl)methoxy]-2-hydroxy-6-[(4-methoxyphenyl)meth oxy]-3,5,7,9-tetramethyl-10-undecenyl]-, dimethyl ester

Chemical Property:

Purity/Quality:

99.90% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Phosphonic acid, [8-[(3,4-dimethoxyphenyl)methoxy]-2-hydroxy-6-[(4-methoxyphenyl)meth oxy]-3,5,7,9-tetramethyl-10-undecenyl]-, dimethyl ester

There total 10 articles about Phosphonic acid, [8-[(3,4-dimethoxyphenyl)methoxy]-2-hydroxy-6-[(4-methoxyphenyl)meth oxy]-3,5,7,9-tetramethyl-10-undecenyl]-, dimethyl 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: 91.0%

(2R,4S,5S,6R,7R,8S)-7-(3,4-dimethoxybenzyloxy)-5-(4-methoxybenzyloxy)-2,4,6,8-tetramethyl-9-hexenal (102852-02-8) + dimethyl methane phosphonate (756-79-6) → [(3R,5S,6S,7R,8R,9S)-8-(3,4-Dimethoxy-benzyloxy)-2-hydroxy-6-(4-methoxy-benzyloxy)-3,5,7,9-tetramethyl-undec-10-enyl]-phosphonic acid dimethyl ester (113956-93-7)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; at -20 ℃; for 8h;

DOI:10.1248/cpb.35.2228

Reference yield:

(2S,3R,5S,6S)-2-isopropyloxy-3,5-dimethyl-6-<1(S)-methyl-2-hydroxyethyl>tetrahydropyran (90093-98-4) → [(3R,5S,6S,7R,8R,9S)-8-(3,4-Dimethoxy-benzyloxy)-2-hydroxy-6-(4-methoxy-benzyloxy)-3,5,7,9-tetramethyl-undec-10-enyl]-phosphonic acid dimethyl ester (113956-93-7)

Guidance literature:

Multi-step reaction with 9 steps

1: 95 percent / Me₂SO, (COCl)2, Et₃N / CH₂Cl₂

2: 94 percent / BF₃-Et₂O / CH₂Cl₂ / -90 °C

3: 95 percent / KCH₂S(O)Me / Ambient temperature

4: 1.) 1 N HCl; 2.) Ca(BH₄)2 / 1.) THF, 50 deg C, 12 h; 2.) EtOH, rt, 3 h

5: CSA / 0.5 h / Ambient temperature

6: KCH₂S(O)Me / dimethylsulfoxide / Ambient temperature

7: 1 N HCl

8: 95 percent / Me₂SO, (COCl)2, Et₃N / CH₂Cl₂

9: 91 percent / n-BuLi / tetrahydrofuran / -80 °C

With hydrogenchloride; n-butyllithium; calcium borohydride; oxalyl dichloride; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; potassium dimsylate; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide;

DOI:10.1021/ja00275a063

Reference yield:

(3S,4R,5S)-4-hydroxy-5(2(S)-isopropyloxy-3(R),5(S)-dimethyl-6(S)-tetrahydroxypropanyl)-3-methylhexane (102851-96-7) → [(3R,5S,6S,7R,8R,9S)-8-(3,4-Dimethoxy-benzyloxy)-2-hydroxy-6-(4-methoxy-benzyloxy)-3,5,7,9-tetramethyl-undec-10-enyl]-phosphonic acid dimethyl ester (113956-93-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 95 percent / KCH₂S(O)Me / Ambient temperature

2: 1.) 1 N HCl; 2.) Ca(BH₄)2 / 1.) THF, 50 deg C, 12 h; 2.) EtOH, rt, 3 h

3: CSA / 0.5 h / Ambient temperature

4: KCH₂S(O)Me / dimethylsulfoxide / Ambient temperature

5: 1 N HCl

6: 95 percent / Me₂SO, (COCl)2, Et₃N / CH₂Cl₂

7: 91 percent / n-BuLi / tetrahydrofuran / -80 °C

With hydrogenchloride; n-butyllithium; calcium borohydride; oxalyl dichloride; camphor-10-sulfonic acid; potassium dimsylate; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide;

DOI:10.1021/ja00275a063

upstream raw materials:

(2R,4S,5S,6R,7R,8S)-7-(3,4-dimethoxybenzyloxy)-5-(4-methoxybenzyloxy)-2,4,6,8-tetramethyl-9-hexenal

dimethyl methane phosphonate

(2S,3R,5S,6S)-2-isopropyloxy-3,5-dimethyl-6-<1(S)-methyl-2-hydroxyethyl>tetrahydropyran

(R)-2-((2S,3S,5R,6S)-6-Isopropoxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-propionaldehyde

Downstream raw materials:

pikronolide

(3R,5R,6S,7S,9R,13R,14R)-14-ethyl-13-benzyloxy-6-(4-methoxybenzyloxy)-3,5,7,9,13-pentamethyl-1-oxacyclotetradec-11(E)-ene-2,4,10-trione

(3R,4S,5R,6S,7S,9R,13R,14R)-13-benzyloxy-14-ethyl-4-hydroxy-6-(4-methoxybenzyloxy)-3,5,7,9,13-pentamethyl-1-oxacyclotetradec-11(E)-ene-2,10-dione

(2R,3S,4R,5S,6S,8R)-3-(3,4-dimethoxybenzyloxy)-10-dimethoxyphosphono-5-(4-methoxybenzyloxy)-2,4,6,8-tetramethyl-9-oxo-decanal

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