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

Base Information

Chemical Name:2-[((3aR,5R,6S,6aR)-6-Acetylamino-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl)-benzyloxycarbonyl-amino]-3-phenyl-propionic acid methyl ester
CAS No.:196868-15-2
Molecular Formula:C₂₈H₃₄N₂O₈
Molecular Weight:526.587
Hs Code.:

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

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

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

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

There total 12 articles about 2-[((3aR,5R,6S,6aR)-6-Acetylamino-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl)-benzyloxycarbonyl-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:

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

: 196868-15-2
2-[((3aR,5R,6S,6aR)-6-Acetylamino-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl)-benzyloxycarbonyl-amino]-3-phenyl-propionic acid methyl ester

Guidance literature:: Multi-step reaction with 5 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

3: 77 percent / aq. Na₂CO₃ / dioxane / 17 h / Ambient temperature

4: NaBH₄ / Pd/C / methanol; H₂O / 0.75 h / Ambient temperature

5: pyridine / 17 h / Ambient temperature

With pyridine; sodium tetrahydroborate; 2,6-di-tert-butyl-4-methylpyridine; sodium carbonate; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; water;
DOI:10.1021/jo9708497

Reference yield:

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

: 196868-15-2
2-[((3aR,5R,6S,6aR)-6-Acetylamino-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl)-benzyloxycarbonyl-amino]-3-phenyl-propionic acid methyl ester

Guidance literature:: Multi-step reaction with 11 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

9: 77 percent / aq. Na₂CO₃ / dioxane / 17 h / Ambient temperature

10: NaBH₄ / Pd/C / methanol; H₂O / 0.75 h / Ambient temperature

11: pyridine / 17 h / Ambient temperature

With pyridine; sodium tetrahydroborate; sodium azide; 2,6-di-tert-butyl-4-methylpyridine; oxalyl dichloride; sodium carbonate; acetic acid; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water;
DOI:10.1021/jo9708497

Reference yield:

: 85951-12-8
1,2-O-isopropylidene-5-O-(tert-butyl)dimethylsilyl-α-D-xylofuranoside

: 196868-15-2
2-[((3aR,5R,6S,6aR)-6-Acetylamino-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl)-benzyloxycarbonyl-amino]-3-phenyl-propionic acid methyl ester

Guidance literature:: Multi-step reaction with 10 steps

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

2: 95 percent / NaBH₄ / ethanol; H₂O / 3.5 h / 0 - 5 °C

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

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

5: 95 percent / CH₃COOH / tetrahydrofuran; H₂O / 18 h / Ambient temperature

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

7: 80 percent / tetrahydrofuran / 14.5 h / Ambient temperature

8: 77 percent / aq. Na₂CO₃ / dioxane / 17 h / Ambient temperature

9: NaBH₄ / Pd/C / methanol; H₂O / 0.75 h / Ambient temperature

10: pyridine / 17 h / Ambient temperature

With pyridine; sodium tetrahydroborate; sodium azide; 2,6-di-tert-butyl-4-methylpyridine; oxalyl dichloride; sodium carbonate; acetic acid; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; water;
DOI:10.1021/jo9708497