2-[((3aR,5R,6S,6aR)-6-Azido-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl)-amino]-3-phenyl-propionic acid methyl ester

Base Information

Chemical Name:2-[((3aR,5R,6S,6aR)-6-Azido-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl)-amino]-3-phenyl-propionic acid methyl ester
CAS No.:196868-11-8
Molecular Formula:C₁₈H₂₄N₄O₅
Molecular Weight:376.412
Hs Code.:

Synonyms:2-[((3aR,5R,6S,6aR)-6-Azido-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl)-amino]-3-phenyl-propionic acid methyl ester

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Chemical Property of 2-[((3aR,5R,6S,6aR)-6-Azido-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl)-amino]-3-phenyl-propionic acid methyl ester

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Technology Process of 2-[((3aR,5R,6S,6aR)-6-Azido-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl)-amino]-3-phenyl-propionic acid methyl ester

There total 8 articles about 2-[((3aR,5R,6S,6aR)-6-Azido-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl)-amino]-3-phenyl-propionic 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: 80.0%

: 15028-44-1
DL-phenylalanine methyl ester

: 196868-09-4
Trifluoro-methanesulfonic acid (3aR,5S,6S,6aR)-6-azido-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl ester

: 196868-11-8
2-[((3aR,5R,6S,6aR)-6-Azido-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl)-amino]-3-phenyl-propionic acid methyl ester

Guidance literature:: In tetrahydrofuran; for 14.5h; Ambient temperature;
DOI:10.1021/jo9708497

Reference yield:

: 28072-60-8
3-azido-3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose

: 196868-11-8
2-[((3aR,5R,6S,6aR)-6-Azido-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl)-amino]-3-phenyl-propionic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 1.) 4-methyl-2,6-di-tert-butylpyridine / 1) (CH₂Cl)2, -78 deg C, 5 min; 2) (CH₂Cl)2, -10 deg C, 30 min

2: 80 percent / tetrahydrofuran / 14.5 h / Ambient temperature

With 2,6-di-tert-butyl-4-methylpyridine; In tetrahydrofuran;
DOI:10.1021/jo9708497

Reference yield:

: 20031-21-4
1,2-O-isopropylidene-α-D-xylose

: 196868-11-8
2-[((3aR,5R,6S,6aR)-6-Azido-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl)-amino]-3-phenyl-propionic acid methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 88 percent / Et₃N / CH₂Cl₂ / 1) 0 deg C, 30 min; 2) rt, 23 h

2: 1.) Oxalyl chloride, DMSO, 2.) Et₃N / 1) CH₂Cl₂, -50 deg C, 30 min; 2) CH₂Cl₂, -55 deg C, 40 min, rt, 2.5 h

3: 95 percent / NaBH₄ / ethanol; H₂O / 3.5 h / 0 - 5 °C

4: 1.) pyridine / 1) CH₂Cl₂, -10 deg C, 3 min; 2) CH₂Cl₂, -10 deg C, 2.25 h

5: 89 percent / NaN₃ / ethanol / 1) 65-70 deg C, 14 h; 2) reflux, 24 h; 3) rt, 4 d

6: 95 percent / CH₃COOH / tetrahydrofuran; H₂O / 18 h / Ambient temperature

7: 1.) 4-methyl-2,6-di-tert-butylpyridine / 1) (CH₂Cl)2, -78 deg C, 5 min; 2) (CH₂Cl)2, -10 deg C, 30 min

8: 80 percent / tetrahydrofuran / 14.5 h / Ambient temperature

With pyridine; sodium tetrahydroborate; sodium azide; 2,6-di-tert-butyl-4-methylpyridine; oxalyl dichloride; acetic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; water;
DOI:10.1021/jo9708497