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

Base Information

• Chemical Name: methyl (3R-(3α,4α,5β))-O-5-(1R-1-(di-(2-(4-nitrophenyl)ethoxy)phosphinyloxy)-1-(dibromomethyl)-2-methoxy-2-oxoethoxy)-shikimate
• CAS No.: 625091-50-1
• Molecular Formula: C₂₈H₃₁Br₂N₂O₁₅P
• Molecular Weight: 826.34
• Mol file: 625091-50-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 3 articles about methyl (3R-(3α,4α,5β))-O-5-(1R-1-(di-(2-(4-nitrophenyl)ethoxy)phosphinyloxy)-1-(dibromomethyl)-2-methoxy-2-oxoethoxy)-shikimate 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: 26.0%

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 (625091-41-0) → methyl (3S-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 (625091-51-2) + methyl (3R-(3α,4α,5β))-O-5-(1R-1-(di-(2-(4-nitrophenyl)ethoxy)phosphinyloxy)-1-(dibromomethyl)-2-methoxy-2-oxoethoxy)-shikimate (625091-50-1)

Guidance literature:

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; With hydrogenchloride; acetic acid; at 20 ℃; for 36h;

With silica gel; In hexane; ethyl acetate; at 20 ℃; for 15h;

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-(3α,4α,5β))-O-5-(1R-1-(di-(2-(4-nitrophenyl)ethoxy)phosphinyloxy)-1-(dibromomethyl)-2-methoxy-2-oxoethoxy)-shikimate (625091-50-1)

Guidance literature:

Multi-step reaction with 4 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

With pyridine; hydrogenchloride; acetic acid; 3-chloro-benzenecarboperoxoic acid; phosphorus trichloride; In dichloromethane;

DOI:10.1021/ja036627+

Reference yield:

C15H19Br2Cl2O8P → methyl (3R-(3α,4α,5β))-O-5-(1R-1-(di-(2-(4-nitrophenyl)ethoxy)phosphinyloxy)-1-(dibromomethyl)-2-methoxy-2-oxoethoxy)-shikimate (625091-50-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: pyridine / CH₂Cl₂ / 4 h / -78 °C

2.1: 928 mg / m-CPBA / CH₂Cl₂ / 17 h / -78 - 20 °C

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

3.2: 26 percent / silica gel / hexane; ethyl acetate / 15 h / 20 °C

With pyridine; hydrogenchloride; acetic acid; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;

DOI:10.1021/ja036627+

upstream raw materials:

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

Downstream raw materials:

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-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

(3R-(3α,4α,5β))-O-3-phospho-O-5-(1S-1-carboxy-1-(phosphooxy)-ethyl)shikimic acid