(E)-(4R,5R)-4-Benzyloxy-5-formyloxy-2,4-dimethyl-hept-2-enoic acid methyl ester

Base Information

Chemical Name:(E)-(4R,5R)-4-Benzyloxy-5-formyloxy-2,4-dimethyl-hept-2-enoic acid methyl ester
CAS No.:120595-03-1
Molecular Formula:C₁₈H₂₄O₅
Molecular Weight:320.386
Hs Code.:

Synonyms:(E)-(4R,5R)-4-Benzyloxy-5-formyloxy-2,4-dimethyl-hept-2-enoic acid methyl ester

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Chemical Property of (E)-(4R,5R)-4-Benzyloxy-5-formyloxy-2,4-dimethyl-hept-2-enoic acid methyl ester

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Technology Process of (E)-(4R,5R)-4-Benzyloxy-5-formyloxy-2,4-dimethyl-hept-2-enoic acid methyl ester

There total 1 articles about (E)-(4R,5R)-4-Benzyloxy-5-formyloxy-2,4-dimethyl-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:

: 120595-02-0
(2S,3R,4R,5R)-4-Benzyloxy-5-ethyl-4-methyl-tetrahydro-furan-2,3-diol

: 2605-68-7
methyl 2-(triphenylphosphoranylidene)propionate

: 120595-03-1
(E)-(4R,5R)-4-Benzyloxy-5-formyloxy-2,4-dimethyl-hept-2-enoic acid methyl ester

Guidance literature:: With sodium periodate; Yield given. Multistep reaction; 1.) NaIO₄, H₂O, MeOH, room temp, 1 h 2.) benzene, reflux, 20 h;
DOI:10.1016/S0040-4020(01)89819-7

Reference yield: 100.0%

: 120595-03-1
(E)-(4R,5R)-4-Benzyloxy-5-formyloxy-2,4-dimethyl-hept-2-enoic acid methyl ester

: 108469-96-1
(E)-(4R,5R)-4-Benzyloxy-5-hydroxy-2,4-dimethyl-hept-2-enoic acid methyl ester

Guidance literature:: With potassium carbonate; In methanol; for 0.5h; Ambient temperature;
DOI:10.1016/S0040-4020(01)89819-7

Reference yield:

: 120595-03-1
(E)-(4R,5R)-4-Benzyloxy-5-formyloxy-2,4-dimethyl-hept-2-enoic acid methyl ester

: 55350-03-3
aurovertin B

Guidance literature:: Multi-step reaction with 15 steps

1: 100 percent / K₂CO₃ / methanol / 0.5 h / Ambient temperature

2: 88 percent / P₂O₅ / CHCl₃ / 0.5 h / Ambient temperature

3: 100 percent / DIBAL-H / tetrahydrofuran / 1.5 h / -78 °C

4: 90 percent / mCPBA / CH₂Cl₂ / - 30 deg C, 7 h, - 20 deg C, 18 h,

5: 1.) DMSO, oxalyl chloride 2.) Et₃N / 1.) DMSO, oxalyl chloride, CH₂Cl₂, - 50 deg C, 15 min 2.) Et₃N, warm to room temp

6: 93 percent / benzene / 1 h / Ambient temperature

7: 94 percent / TFA / CHCl₃ / 0.17 h / Ambient temperature

8: 100 percent / DIBAL-H / 1 h / -78 °C

9: 82 percent / pyridine / CH₂Cl₂ / 22 h / Ambient temperature

10: pyridine

11: 90 percent / TsOH / methanol / 1 h / Ambient temperature

12: 99 percent / diethyl D-tartrate, Ti(OiPr)4, TBHP / CH₂Cl₂ / 12 h / -20 °C

13: oxalyl chloride,DMSO,Et₃N

14: 14 percent / benzene / 1.5 h / Ambient temperature

15: 22 percent / NaH / tetrahydrofuran / 1.)40 deg C,17 h; 2.)reflux,28 h

With pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; oxalyl dichloride; diethyl (2S,3S)-tartrate; phosphorus pentoxide; sodium hydride; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane; chloroform; benzene;
DOI:10.1016/S0040-4020(01)89819-7