(E)-(4R,5R)-5-[(R)-2-({2-[(4R,6S)-6-((1E,3E)-5-Amino-2-methyl-penta-1,3-dienyl)-2-(2,4,6-trimethyl-phenyl)-[1,3]dioxan-4-ylmethyl]-oxazole-4-carbonyl}-amino)-propionyloxy]-4,6-dimethyl-hept-2-enoic acid

Base Information

Chemical Name:(E)-(4R,5R)-5-[(R)-2-({2-[(4R,6S)-6-((1E,3E)-5-Amino-2-methyl-penta-1,3-dienyl)-2-(2,4,6-trimethyl-phenyl)-[1,3]dioxan-4-ylmethyl]-oxazole-4-carbonyl}-amino)-propionyloxy]-4,6-dimethyl-hept-2-enoic acid
CAS No.:175663-03-3
Molecular Formula:C₃₆H₄₉N₃O₈
Molecular Weight:651.8
Hs Code.:

(E)-(4R,5R)-5-[(R)-2-({2-[(4R,6S)-6-((1E,3E)-5-Amino-2-methyl-penta-1,3-dienyl)-2-(2,4,6-trimethyl-phenyl)-[1,3]dioxan-4-ylmethyl]-oxazole-4-carbonyl}-amino)-propionyloxy]-4,6-dimethyl-hept-2-enoic acid

Synonyms:(E)-(4R,5R)-5-[(R)-2-({2-[(4R,6S)-6-((1E,3E)-5-Amino-2-methyl-penta-1,3-dienyl)-2-(2,4,6-trimethyl-phenyl)-[1,3]dioxan-4-ylmethyl]-oxazole-4-carbonyl}-amino)-propionyloxy]-4,6-dimethyl-hept-2-enoic acid

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Chemical Property of (E)-(4R,5R)-5-[(R)-2-({2-[(4R,6S)-6-((1E,3E)-5-Amino-2-methyl-penta-1,3-dienyl)-2-(2,4,6-trimethyl-phenyl)-[1,3]dioxan-4-ylmethyl]-oxazole-4-carbonyl}-amino)-propionyloxy]-4,6-dimethyl-hept-2-enoic acid

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Technology Process of (E)-(4R,5R)-5-[(R)-2-({2-[(4R,6S)-6-((1E,3E)-5-Amino-2-methyl-penta-1,3-dienyl)-2-(2,4,6-trimethyl-phenyl)-[1,3]dioxan-4-ylmethyl]-oxazole-4-carbonyl}-amino)-propionyloxy]-4,6-dimethyl-hept-2-enoic acid

There total 12 articles about (E)-(4R,5R)-5-[(R)-2-({2-[(4R,6S)-6-((1E,3E)-5-Amino-2-methyl-penta-1,3-dienyl)-2-(2,4,6-trimethyl-phenyl)-[1,3]dioxan-4-ylmethyl]-oxazole-4-carbonyl}-amino)-propionyloxy]-4,6-dimethyl-hept-2-enoic acid 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:

: 175663-02-2
(E)-(4R,5R)-5-[(R)-2-({2-[(4R,6S)-6-((1E,3E)-5-Amino-2-methyl-penta-1,3-dienyl)-2-(2,4,6-trimethyl-phenyl)-[1,3]dioxan-4-ylmethyl]-oxazole-4-carbonyl}-amino)-propionyloxy]-4,6-dimethyl-hept-2-enoic acid 2-trimethylsilanyl-ethyl ester

: 175663-03-3
(E)-(4R,5R)-5-[(R)-2-({2-[(4R,6S)-6-((1E,3E)-5-Amino-2-methyl-penta-1,3-dienyl)-2-(2,4,6-trimethyl-phenyl)-[1,3]dioxan-4-ylmethyl]-oxazole-4-carbonyl}-amino)-propionyloxy]-4,6-dimethyl-hept-2-enoic acid

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 25 ℃; for 4h;
DOI:10.1021/ja954312r

Reference yield:

: 64761-29-1
mesitaldehyde dimethylacetal

: 175663-03-3
(E)-(4R,5R)-5-[(R)-2-({2-[(4R,6S)-6-((1E,3E)-5-Amino-2-methyl-penta-1,3-dienyl)-2-(2,4,6-trimethyl-phenyl)-[1,3]dioxan-4-ylmethyl]-oxazole-4-carbonyl}-amino)-propionyloxy]-4,6-dimethyl-hept-2-enoic acid

Guidance literature:: Multi-step reaction with 8 steps

1: 74 percent / camphorsulfonic acid / CH₂Cl₂ / 48 h / 0 °C

2: 86 percent / SO₃*pyridine, Et₃N / dimethylsulfoxide

3: 82 percent / benzene / 23 h / Heating

4: 61 percent / tetrahydrofuran / 48 h / 65 °C / Heating

5: 93 percent / pyridine / 11 h / Heating

6: 63 percent / DCC, DMAP / CH₂Cl₂ / 9 h / 0 - 25 °C

7: 78 percent / CH₃NH₂ / ethanol; benzene / 48 h / 50 °C

8: Bu₄NF / tetrahydrofuran / 4 h / 0 - 25 °C

With pyridine; dmap; pyridine-SO₃ complex; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; triethylamine; dicyclohexyl-carbodiimide; methylamine; In tetrahydrofuran; ethanol; dichloromethane; dimethyl sulfoxide; benzene;
DOI:10.1021/ja954312r

Reference yield:

: 77877-21-5
(4S)-3-((2S,3R)-3-hydroxy-2,4-dimethyl-1-oxopentyl)-4-(1-methylethyl)-2-oxazolidinone

: 175663-03-3
(E)-(4R,5R)-5-[(R)-2-({2-[(4R,6S)-6-((1E,3E)-5-Amino-2-methyl-penta-1,3-dienyl)-2-(2,4,6-trimethyl-phenyl)-[1,3]dioxan-4-ylmethyl]-oxazole-4-carbonyl}-amino)-propionyloxy]-4,6-dimethyl-hept-2-enoic acid

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) Me₃Al, MeNH(OMe)*HCl, 2.) DIBAH / 1.) CH₂Cl₂, 0 deg C, 3 h, 2.) toluene, -78 deg C, 30 min

2: LiCl, i-PrEt₂N / acetonitrile

3: 100 percent / DCC / CH₂Cl₂ / 11 h / 0 - 20 °C

4: 83 percent / TsOH*H₂O / 16 h / 23 °C

5: 63 percent / DCC, DMAP / CH₂Cl₂ / 9 h / 0 - 25 °C

6: 78 percent / CH₃NH₂ / ethanol; benzene / 48 h / 50 °C

7: Bu₄NF / tetrahydrofuran / 4 h / 0 - 25 °C

With dmap; N,N-diethyl-N-isopropylamine; tetrabutyl ammonium fluoride; trimethylaluminum; N,O-dimethylhydroxylamine*hydrochloride; diisobutylaluminium hydride; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide; methylamine; lithium chloride; In tetrahydrofuran; ethanol; dichloromethane; acetonitrile; benzene;
DOI:10.1021/ja954312r