(R)-4-Benzyloxy-4-[(4R,5S,6R)-2,2,5-trimethyl-6-((S)-1-methyl-allyl)-[1,3]dioxan-4-yl]-pentanoic acid methoxymethyl ester

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Chemical Name:(R)-4-Benzyloxy-4-[(4R,5S,6R)-2,2,5-trimethyl-6-((S)-1-methyl-allyl)-[1,3]dioxan-4-yl]-pentanoic acid methoxymethyl ester
CAS No.:123219-53-4
Molecular Formula:C₂₅H₃₈O₆
Molecular Weight:434.573
Hs Code.:

Synonyms:(R)-4-Benzyloxy-4-[(4R,5S,6R)-2,2,5-trimethyl-6-((S)-1-methyl-allyl)-[1,3]dioxan-4-yl]-pentanoic acid methoxymethyl ester

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Chemical Property of (R)-4-Benzyloxy-4-[(4R,5S,6R)-2,2,5-trimethyl-6-((S)-1-methyl-allyl)-[1,3]dioxan-4-yl]-pentanoic acid methoxymethyl ester

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Technology Process of (R)-4-Benzyloxy-4-[(4R,5S,6R)-2,2,5-trimethyl-6-((S)-1-methyl-allyl)-[1,3]dioxan-4-yl]-pentanoic acid methoxymethyl ester

There total 13 articles about (R)-4-Benzyloxy-4-[(4R,5S,6R)-2,2,5-trimethyl-6-((S)-1-methyl-allyl)-[1,3]dioxan-4-yl]-pentanoic acid methoxymethyl 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: 92.3%

: (R)-4-Benzyloxy-4-[(4R,5S,6R)-2,2,5-trimethyl-6-((S)-1-methyl-allyl)-[1,3]dioxan-4-yl]-pentanoic acid

: 107-30-2
chloromethyl methyl ether

: 123219-53-4
(R)-4-Benzyloxy-4-[(4R,5S,6R)-2,2,5-trimethyl-6-((S)-1-methyl-allyl)-[1,3]dioxan-4-yl]-pentanoic acid methoxymethyl ester

Guidance literature:: With 1,5-Diazabicyclo[5.4.0]undec-5-ene; In acetonitrile; at 20 ℃; for 0.5h;
DOI:10.1007/BF00953720

Reference yield:

: (2S,3S,4S,5R)-5-[1,3]Dithiolan-2-yl-3-methyl-hexane-1,2,4-triol

: 123219-53-4
(R)-4-Benzyloxy-4-[(4R,5S,6R)-2,2,5-trimethyl-6-((S)-1-methyl-allyl)-[1,3]dioxan-4-yl]-pentanoic acid methoxymethyl ester

Guidance literature:: Multi-step reaction with 12 steps

1: CH₂Cl₂; pyridine / 2 h / -10 °C

2: TsOH*H₂O / acetone / 0.5 h / 20 °C

3: 77 percent / CaCO₃, HgCl₂ / acetonitrile; H₂O / 84 h / 20 °C

4: 1) n-BuLi, 2) CH₃ONa / 1) a) hexane/benzene, ca. 20 deg C, 10 min, b) reflux, 10 min, 2) CH₃OH, 30 min

5: DMSO, (COCl)2, triethylamine / CH₂Cl₂ / 0.42 h / -60 °C

6: tetrahydrofuran / 0.5 h / 20 °C

7: 95 percent / K₂CO₃ / methanol / 1 h / 20 °C

8: 85.2 percent / tetrahydrofuran / 1) -70 deg C, 10 min, 2) 20 deg C

9: 89 percent / 1) NaH / dimethylformamide / 20 °C / 1) 30 min, 2) 4 h

10: 62 percent / 1) ozone, 2) dimethyl sulfide / pyridine; CH₂Cl₂ / 1) -70 deg C, 2) ca. 20 deg C, 1 h

11: m-chloroperbenzoic acid / tetrahydrofuran; H₂O / 0.08 h / 20 °C / phosphate buffer (pH: 7.0)

12: 92.3 percent / 1,5-diazabicyclo<5.4.0>undec-5-ene / acetonitrile / 0.5 h / 20 °C

With n-butyllithium; oxalyl dichloride; dimethylsulfide; sodium methylate; sodium hydride; potassium carbonate; ozone; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; calcium carbonate; mercury dichloride; 1,5-Diazabicyclo[5.4.0]undec-5-ene; toluene-4-sulfonic acid; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile;
DOI:10.1007/BF00953720

Reference yield:

: 123219-60-3
Acetic acid (2S,3S,4S,5R)-5-[1,3]dithiolan-2-yl-2,4-dihydroxy-3-methyl-hexyl ester

: 123219-53-4
(R)-4-Benzyloxy-4-[(4R,5S,6R)-2,2,5-trimethyl-6-((S)-1-methyl-allyl)-[1,3]dioxan-4-yl]-pentanoic acid methoxymethyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: TsOH*H₂O / acetone / 0.5 h / 20 °C

2: 77 percent / CaCO₃, HgCl₂ / acetonitrile; H₂O / 84 h / 20 °C

3: 1) n-BuLi, 2) CH₃ONa / 1) a) hexane/benzene, ca. 20 deg C, 10 min, b) reflux, 10 min, 2) CH₃OH, 30 min

4: DMSO, (COCl)2, triethylamine / CH₂Cl₂ / 0.42 h / -60 °C

5: tetrahydrofuran / 0.5 h / 20 °C

6: 95 percent / K₂CO₃ / methanol / 1 h / 20 °C

7: 85.2 percent / tetrahydrofuran / 1) -70 deg C, 10 min, 2) 20 deg C

8: 89 percent / 1) NaH / dimethylformamide / 20 °C / 1) 30 min, 2) 4 h

9: 62 percent / 1) ozone, 2) dimethyl sulfide / pyridine; CH₂Cl₂ / 1) -70 deg C, 2) ca. 20 deg C, 1 h

10: m-chloroperbenzoic acid / tetrahydrofuran; H₂O / 0.08 h / 20 °C / phosphate buffer (pH: 7.0)

11: 92.3 percent / 1,5-diazabicyclo<5.4.0>undec-5-ene / acetonitrile / 0.5 h / 20 °C

With n-butyllithium; oxalyl dichloride; dimethylsulfide; sodium methylate; sodium hydride; potassium carbonate; ozone; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; calcium carbonate; mercury dichloride; 1,5-Diazabicyclo[5.4.0]undec-5-ene; toluene-4-sulfonic acid; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile;
DOI:10.1007/BF00953720