(2R,3R,4S,4aR)-2-Hydroxy-5-(4-methoxybenzyl)-3,4-bis<(methoxymethyl)oxy>-3,4,4a,5-tetrahydro<1,3>dioxolo<4,5-j>phenanthridin-6(2H)-one

Base Information

• Chemical Name: (2R,3R,4S,4aR)-2-Hydroxy-5-(4-methoxybenzyl)-3,4-bis<(methoxymethyl)oxy>-3,4,4a,5-tetrahydro<1,3>dioxolo<4,5-j>phenanthridin-6(2H)-one
• CAS No.: 137423-24-6
• Molecular Formula: C₂₆H₂₉NO₉
• Molecular Weight: 499.518
• Mol file: 137423-24-6.mol

Synonyms:(2R,3R,4S,4aR)-2-Hydroxy-5-(4-methoxybenzyl)-3,4-bis<(methoxymethyl)oxy>-3,4,4a,5-tetrahydro<1,3>dioxolo<4,5-j>phenanthridin-6(2H)-one

Chemical Property of (2R,3R,4S,4aR)-2-Hydroxy-5-(4-methoxybenzyl)-3,4-bis<(methoxymethyl)oxy>-3,4,4a,5-tetrahydro<1,3>dioxolo<4,5-j>phenanthridin-6(2H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4S,4aR)-2-Hydroxy-5-(4-methoxybenzyl)-3,4-bis<(methoxymethyl)oxy>-3,4,4a,5-tetrahydro<1,3>dioxolo<4,5-j>phenanthridin-6(2H)-one

There total 12 articles about (2R,3R,4S,4aR)-2-Hydroxy-5-(4-methoxybenzyl)-3,4-bis<(methoxymethyl)oxy>-3,4,4a,5-tetrahydro<1,3>dioxolo<4,5-j>phenanthridin-6(2H)-one 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: 53.0%

(2R,3R,4S,4aR)-5-(4-Methoxybenzyl)-2-<(4-methoxybenzyl)oxy>-3,4-bis<(methoxymethyl)oxy>-3,4,4a,5-tetrahydro<1,3>dioxolo<4,5-j>phenanthridin-6(2H)-one (137423-23-5) → (2R,3R,4S,4aR)-2-Hydroxy-5-(4-methoxybenzyl)-3,4-bis<(methoxymethyl)oxy>-3,4,4a,5-tetrahydro<1,3>dioxolo<4,5-j>phenanthridin-6(2H)-one (137423-24-6)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water;

DOI:10.1016/0040-4039(91)80030-A

Reference yield:

6-bromopiperonylic acid (60546-62-5) → (2R,3R,4S,4aR)-2-Hydroxy-5-(4-methoxybenzyl)-3,4-bis<(methoxymethyl)oxy>-3,4,4a,5-tetrahydro<1,3>dioxolo<4,5-j>phenanthridin-6(2H)-one (137423-24-6)

Guidance literature:

Multi-step reaction with 4 steps

1: diethyl cyanophosphonate, Et₃N / dimethylformamide / 0.25 h / 0 °C

2: 1) NaH / 1) DMF, 0 deg C, 30 min, 2) r.t., 5 h

3: 68 percent / TlOAc / Pd(OAc)2, 1,2-bis(diphenylphosphino)ethane / dimethylformamide / 7 h / 140 °C

4: 53 percent / DDQ / CH₂Cl₂ / 3 h / 0 °C

With diethyl cyanophosphonate; thallium(I) acetate; sodium hydride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium diacetate; 1,2-bis-(diphenylphosphino)ethane; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00068a045

Reference yield:

methyl 2-amino-6-bromo-2,6-dideoxy-α-D-altropyranoside (53437-75-5) → (2R,3R,4S,4aR)-2-Hydroxy-5-(4-methoxybenzyl)-3,4-bis<(methoxymethyl)oxy>-3,4,4a,5-tetrahydro<1,3>dioxolo<4,5-j>phenanthridin-6(2H)-one (137423-24-6)

Guidance literature:

Multi-step reaction with 10 steps

1: 1) iPr₂NEt, 2) DBU / 1) CH₂Cl₂, 15 h, reflux, 2) toluene, 15 h, reflux

2: 5.75 g / Hg(OCOCF₃)2 / acetone; H₂O / 20 h / Ambient temperature

3: 69 percent / Et₃N, MeSO₂Cl / CH₂Cl₂ / 1.5 h / 0 °C

4: 86 percent / CeCl₃*7H₂O, NaBH₄ / methanol / 0.5 h / 0 °C

5: 1) NaH / 1) DMF, 0 deg C, 30 min, 2) r.t., 18 h

6: LiAlH₄ / diethyl ether / 0.5 h / 0 °C

7: diethyl cyanophosphonate, Et₃N / dimethylformamide / 0.25 h / 0 °C

8: 1) NaH / 1) DMF, 0 deg C, 30 min, 2) r.t., 5 h

9: 68 percent / TlOAc / Pd(OAc)2, 1,2-bis(diphenylphosphino)ethane / dimethylformamide / 7 h / 140 °C

10: 53 percent / DDQ / CH₂Cl₂ / 3 h / 0 °C

With sodium tetrahydroborate; lithium aluminium tetrahydride; cerium(III) chloride; diethyl cyanophosphonate; thallium(I) acetate; sodium hydride; methanesulfonyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium diacetate; mercury(II) trifluoroacetate; 1,2-bis-(diphenylphosphino)ethane; In methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone;

DOI:10.1021/jo00068a045

upstream raw materials:

(2R,3R,4S,4aR)-5-(4-Methoxybenzyl)-2-<(4-methoxybenzyl)oxy>-3,4-bis<(methoxymethyl)oxy>-3,4,4a,5-tetrahydro<1,3>dioxolo<4,5-j>phenanthridin-6(2H)-one

6-bromopiperonylic acid

methyl 2-amino-6-bromo-2,6-dideoxy-α-D-altropyranoside

2L-(2,3/4)-4-Azido-2,3-bis-O-(methoxymethyl)-2,3-dihydroxy-5-cyclohexen-1-one

Downstream raw materials:

(2S,3R,4S,4aR)-2-(Benzoyloxy)-5-(4-methoxybenzyl)-3,4-bis<(methoxymethyl)oxy>-3,4,4a,5-tetrahydro<1,3>dioxolo<4,5-j>phenanthridin-6(2H)-one

(2S,3R,4S,4aR)-2,3,4-Triacetoxy-5-(4-methoxybenzyl)-3,4,4a,5-tetrahydro<1,3>dioxolo<4,5-j>phenanthridin-6(2H)-one

(2S,3R,4S,4aR)-2-Hydroxy-5-(4-methoxybenzyl)-3,4-bis<(methoxymethyl)oxy>-3,4,4a,5-tetrahydro<1,3>dioxolo<4,5-j>phenanthridin-6(2H)-one

(2R,3R,4S,4aR)-2,3,4-Triacetoxy-5-(4-methoxybenzyl)-3,4,4a,5-tetrahydro<1,3>dioxolo<4,5-j>phenanthridin-6(2H)-one