(E)-(4R,5S,6R)-4-Benzyloxycarbonylamino-6-hydroxy-7-trityloxy-5-trityloxymethyl-hept-2-enoic acid methyl ester

Base Information

• Chemical Name: (E)-(4R,5S,6R)-4-Benzyloxycarbonylamino-6-hydroxy-7-trityloxy-5-trityloxymethyl-hept-2-enoic acid methyl ester
• CAS No.: 85781-37-9
• Molecular Formula: C₅₅H₅₁NO₇
• Molecular Weight: 838.012
• Mol file: 85781-37-9.mol

Synonyms:(E)-(4R,5S,6R)-4-Benzyloxycarbonylamino-6-hydroxy-7-trityloxy-5-trityloxymethyl-hept-2-enoic acid methyl ester

Chemical Property of (E)-(4R,5S,6R)-4-Benzyloxycarbonylamino-6-hydroxy-7-trityloxy-5-trityloxymethyl-hept-2-enoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(4R,5S,6R)-4-Benzyloxycarbonylamino-6-hydroxy-7-trityloxy-5-trityloxymethyl-hept-2-enoic acid methyl ester

There total 5 articles about (E)-(4R,5S,6R)-4-Benzyloxycarbonylamino-6-hydroxy-7-trityloxy-5-trityloxymethyl-hept-2-enoic acid methyl 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: 85.0%

((3R,4S,5S)-2-Hydroxy-4,5-bis-trityloxymethyl-tetrahydro-furan-3-yl)-carbamic acid benzyl ester (85781-36-8) + methyl (triphenylphosphoranylidene)acetate (21204-67-1,2605-67-6) → (E)-(4R,5S,6R)-4-Benzyloxycarbonylamino-6-hydroxy-7-trityloxy-5-trityloxymethyl-hept-2-enoic acid methyl ester (85781-37-9)

Guidance literature:

In toluene; at 60 ℃; for 62h;

DOI:10.1021/ja00350a061

Reference yield:

trityl chloride (76-83-5) → (E)-(4R,5S,6R)-4-Benzyloxycarbonylamino-6-hydroxy-7-trityloxy-5-trityloxymethyl-hept-2-enoic acid methyl ester (85781-37-9)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / 26 h / 70 °C

2: 85 percent / toluene / 62 h / 60 °C

With pyridine; In toluene;

DOI:10.1021/ja00350a061

Reference yield:

methyl 2-amino-2,3-dideoxy-3-C-formyl-α-D-xylofuranoside-(3'R)-5-hemiacetal (84034-70-8) → (E)-(4R,5S,6R)-4-Benzyloxycarbonylamino-6-hydroxy-7-trityloxy-5-trityloxymethyl-hept-2-enoic acid methyl ester (85781-37-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 2.) NaBH₄ / 1.) MeOH(aq), 1.5 h, 2.) MeOH

2: pyridine / 26 h / 70 °C

3: 85 percent / toluene / 62 h / 60 °C

With pyridine; sodium tetrahydroborate; In toluene;

DOI:10.1021/ja00350a061

upstream raw materials:

((3R,4S,5S)-2-Hydroxy-4,5-bis-trityloxymethyl-tetrahydro-furan-3-yl)-carbamic acid benzyl ester

methyl (triphenylphosphoranylidene)acetate

trityl chloride

methyl 2-amino-2,3-dideoxy-3-C-formyl-α-D-xylofuranoside-(3'R)-5-hemiacetal