(S)-3-((2S,4S,5R,6R)-6-Benzyloxymethoxy-4,5-bis-methoxymethoxy-2-methyl-oct-7-enoyl)-4-isopropyl-oxazolidin-2-one

Base Information

Chemical Name:(S)-3-((2S,4S,5R,6R)-6-Benzyloxymethoxy-4,5-bis-methoxymethoxy-2-methyl-oct-7-enoyl)-4-isopropyl-oxazolidin-2-one
CAS No.:269076-53-1
Molecular Formula:C₂₇H₄₁NO₉
Molecular Weight:523.624
Hs Code.:

Synonyms:(S)-3-((2S,4S,5R,6R)-6-Benzyloxymethoxy-4,5-bis-methoxymethoxy-2-methyl-oct-7-enoyl)-4-isopropyl-oxazolidin-2-one

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Chemical Property of (S)-3-((2S,4S,5R,6R)-6-Benzyloxymethoxy-4,5-bis-methoxymethoxy-2-methyl-oct-7-enoyl)-4-isopropyl-oxazolidin-2-one

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Technology Process of (S)-3-((2S,4S,5R,6R)-6-Benzyloxymethoxy-4,5-bis-methoxymethoxy-2-methyl-oct-7-enoyl)-4-isopropyl-oxazolidin-2-one

There total 10 articles about (S)-3-((2S,4S,5R,6R)-6-Benzyloxymethoxy-4,5-bis-methoxymethoxy-2-methyl-oct-7-enoyl)-4-isopropyl-oxazolidin-2-one 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: 77.0%

: 269076-47-3
(S)-3-((4S,5R,6R)-6-Benzyloxymethoxy-4,5-bis-methoxymethoxy-oct-7-enoyl)-4-isopropyl-oxazolidin-2-one

: 74-88-4
methyl iodide

: 269076-53-1
(S)-3-((2S,4S,5R,6R)-6-Benzyloxymethoxy-4,5-bis-methoxymethoxy-2-methyl-oct-7-enoyl)-4-isopropyl-oxazolidin-2-one

Guidance literature:: With lithium diisopropyl amide; In tetrahydrofuran; at -78 - -40 ℃; for 22h;
DOI:10.1016/S0040-4039(00)00062-9

Reference yield:

: (4aR,6S,7R,8S,8aR)-6-Methoxy-7,8-bis-methoxymethoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

: 269076-53-1
(S)-3-((2S,4S,5R,6R)-6-Benzyloxymethoxy-4,5-bis-methoxymethoxy-2-methyl-oct-7-enoyl)-4-isopropyl-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 9 steps

1: NBS; BaCO₃ / AIBN / CCl₄ / 1 h / reflux

2: Zn / ethanol; H₂O / 3 h / reflux

3: benzene / 23 h / 23 °C

4: NaBH₄; CuCl₂ / methanol / 3 h / 23 °C

5: NaOMe / methanol / 7 h / 23 °C

6: 88 percent / (i-Pr)2EtN / CH₂Cl₂ / 48 h / 23 °C

7: 92 percent / NaOH / methanol; H₂O / 18 h / 0 °C

8: 97 percent / PivCl; Et₃N; LiCl / tetrahydrofuran / 6.5 h / -20 - 23 °C

9: 77 percent / LDA / tetrahydrofuran / 22 h / -78 - -40 °C

With sodium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; sodium methylate; pivaloyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; barium carbonate; lithium chloride; copper dichloride; zinc; lithium diisopropyl amide; 2,2'-azobis(isobutyronitrile); In tetrahydrofuran; methanol; tetrachloromethane; ethanol; dichloromethane; water; benzene; 1: Bromination / 2: Ring cleavage / 3: Condensation / 4: Reduction / 5: Hydrolysis / 6: Alkylation / 7: Hydrolysis / 8: Acylation / 9: Methylation;
DOI:10.1016/S0040-4039(00)00062-9

Reference yield:

: 3587-60-8
Benzyloxymethyl chloride

: 269076-53-1
(S)-3-((2S,4S,5R,6R)-6-Benzyloxymethoxy-4,5-bis-methoxymethoxy-2-methyl-oct-7-enoyl)-4-isopropyl-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 4 steps

1: 88 percent / (i-Pr)2EtN / CH₂Cl₂ / 48 h / 23 °C

2: 92 percent / NaOH / methanol; H₂O / 18 h / 0 °C

3: 97 percent / PivCl; Et₃N; LiCl / tetrahydrofuran / 6.5 h / -20 - 23 °C

4: 77 percent / LDA / tetrahydrofuran / 22 h / -78 - -40 °C

With sodium hydroxide; pivaloyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; water; 1: Alkylation / 2: Hydrolysis / 3: Acylation / 4: Methylation;
DOI:10.1016/S0040-4039(00)00062-9