methyl (3R-4aR-(4aβ,8α,8aα))-3-(di-(2-(4-nitrophenyl)ethoxy)phosphinyloxy)-8-(di-(2-(4-nitrophenyl)ethoxy)phosphinyloxy)-3-(dibromomethyl)-2-oxo-2,3,4a,5,8,8a-hexahydro-1,4-benzodioxin-6-carboxylate

Base Information

• Chemical Name: methyl (3R-4aR-(4aβ,8α,8aα))-3-(di-(2-(4-nitrophenyl)ethoxy)phosphinyloxy)-8-(di-(2-(4-nitrophenyl)ethoxy)phosphinyloxy)-3-(dibromomethyl)-2-oxo-2,3,4a,5,8,8a-hexahydro-1,4-benzodioxin-6-carboxylate
• CAS No.: 625091-55-6
• Molecular Formula: C₄₃H₄₂Br₂N₄O₂₁P₂
• Molecular Weight: 1172.58
• Mol file: 625091-55-6.mol

Synonyms:methyl (3R-4aR-(4aβ,8α,8aα))-3-(di-(2-(4-nitrophenyl)ethoxy)phosphinyloxy)-8-(di-(2-(4-nitrophenyl)ethoxy)phosphinyloxy)-3-(dibromomethyl)-2-oxo-2,3,4a,5,8,8a-hexahydro-1,4-benzodioxin-6-carboxylate

Chemical Property of methyl (3R-4aR-(4aβ,8α,8aα))-3-(di-(2-(4-nitrophenyl)ethoxy)phosphinyloxy)-8-(di-(2-(4-nitrophenyl)ethoxy)phosphinyloxy)-3-(dibromomethyl)-2-oxo-2,3,4a,5,8,8a-hexahydro-1,4-benzodioxin-6-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (3R-4aR-(4aβ,8α,8aα))-3-(di-(2-(4-nitrophenyl)ethoxy)phosphinyloxy)-8-(di-(2-(4-nitrophenyl)ethoxy)phosphinyloxy)-3-(dibromomethyl)-2-oxo-2,3,4a,5,8,8a-hexahydro-1,4-benzodioxin-6-carboxylate

There total 8 articles about methyl (3R-4aR-(4aβ,8α,8aα))-3-(di-(2-(4-nitrophenyl)ethoxy)phosphinyloxy)-8-(di-(2-(4-nitrophenyl)ethoxy)phosphinyloxy)-3-(dibromomethyl)-2-oxo-2,3,4a,5,8,8a-hexahydro-1,4-benzodioxin-6-carboxylate 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:

(3R,4aR,8R,8aS)-8-{Bis-[2-(4-nitro-phenyl)-ethoxy]-phosphanyloxy}-3-{bis-[2-(4-nitro-phenyl)-ethoxy]-phosphoryloxy}-3-dibromomethyl-2-oxo-2,3,4a,5,8,8a-hexahydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester → methyl (3R-4aR-(4aβ,8α,8aα))-3-(di-(2-(4-nitrophenyl)ethoxy)phosphinyloxy)-8-(di-(2-(4-nitrophenyl)ethoxy)phosphinyloxy)-3-(dibromomethyl)-2-oxo-2,3,4a,5,8,8a-hexahydro-1,4-benzodioxin-6-carboxylate (625091-55-6)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; for 1h;

DOI:10.1021/ja036627+

Reference yield:

bis(2-<4-nitrophenyl>ethyl) N,N-diisopropylphosphoramidite (102690-87-9) → methyl (3R-4aR-(4aβ,8α,8aα))-3-(di-(2-(4-nitrophenyl)ethoxy)phosphinyloxy)-8-(di-(2-(4-nitrophenyl)ethoxy)phosphinyloxy)-3-(dibromomethyl)-2-oxo-2,3,4a,5,8,8a-hexahydro-1,4-benzodioxin-6-carboxylate (625091-55-6)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrazole / tetrahydrofuran / 4.5 h / 20 °C

2: 365 mg / m-CPBA / tetrahydrofuran; CH₂Cl₂ / 1 h

With 1H-tetrazole; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja036627+

Reference yield:

(3aR,7R,7aS)-7-(2,2-Dibromo-1-hydroxy-1-methoxycarbonyl-ethoxy)-2,2-dimethyl-3a,6,7,7a-tetrahydro-benzo[1,3]dioxole-5-carboxylic acid methyl ester → methyl (3R-4aR-(4aβ,8α,8aα))-3-(di-(2-(4-nitrophenyl)ethoxy)phosphinyloxy)-8-(di-(2-(4-nitrophenyl)ethoxy)phosphinyloxy)-3-(dibromomethyl)-2-oxo-2,3,4a,5,8,8a-hexahydro-1,4-benzodioxin-6-carboxylate (625091-55-6)

Guidance literature:

Multi-step reaction with 7 steps

1.1: PCl₃; pyridine / CH₂Cl₂ / 0.5 h / -78 °C

2.1: pyridine / CH₂Cl₂ / 4 h / -78 °C

3.1: 928 mg / m-CPBA / CH₂Cl₂ / 17 h / -78 - 20 °C

4.1: aq. HCl; acetic acid / 36 h / 20 °C

4.2: 26 percent / silica gel / hexane; ethyl acetate / 15 h / 20 °C

5.1: 66 percent / K₂CO₃; silica gel; Ms 4Ae / acetonitrile / 17 h / 20 °C

6.1: tetrazole / tetrahydrofuran / 4.5 h / 20 °C

7.1: 365 mg / m-CPBA / tetrahydrofuran; CH₂Cl₂ / 1 h

With pyridine; 1H-tetrazole; hydrogenchloride; silica gel; potassium carbonate; acetic acid; 3-chloro-benzenecarboperoxoic acid; phosphorus trichloride; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1021/ja036627+

upstream raw materials:

bis(2-<4-nitrophenyl>ethyl) N,N-diisopropylphosphoramidite

methyl (3R-4aR-(4aβ,8α,8aα))-3-(di-(2-(4-nitrophenyl)ethoxy)phosphinyloxy)-3-(dibromomethyl)-8-hydroxy-2-oxo-2,3,4a,5,8,8a-hexahydro-1,4-benzodioxin-6-carboxylate

methyl (3R-(3α,4α,5β))-O-5-(1R-1-(di-(2-(4-nitrophenyl)ethoxy)phosphinyloxy)-1-(dibromomethyl)-2-methoxy-2-oxoethoxy)-shikimate

methyl (3aR-(3aα,7β,7aα))-7-(bis(2-(4-nitrophenyl)ethoxy)phosphinyloxy-1-(dibromomethyl)-2-methoxy-2-oxoethoxy)-2,2-dimethyl-3a,6,7,7a-tetrahydro-1,3-benzodioxole-5-carboxylate