(S)-4-benzyl-3-((2S,3R,8S,9R,E)-3-hydroxy-9-((4-methoxybenzyl)oxy)-8-(methoxymethoxy)-2-methyltetradec-4-enoyl)oxazolidin-2-one

Base Information

Chemical Name:(S)-4-benzyl-3-((2S,3R,8S,9R,E)-3-hydroxy-9-((4-methoxybenzyl)oxy)-8-(methoxymethoxy)-2-methyltetradec-4-enoyl)oxazolidin-2-one
CAS No.:1609652-05-2
Molecular Formula:C₃₅H₄₉NO₈
Molecular Weight:611.776
Hs Code.:

Synonyms:(S)-4-benzyl-3-((2S,3R,8S,9R,E)-3-hydroxy-9-((4-methoxybenzyl)oxy)-8-(methoxymethoxy)-2-methyltetradec-4-enoyl)oxazolidin-2-one

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Chemical Property of (S)-4-benzyl-3-((2S,3R,8S,9R,E)-3-hydroxy-9-((4-methoxybenzyl)oxy)-8-(methoxymethoxy)-2-methyltetradec-4-enoyl)oxazolidin-2-one

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Technology Process of (S)-4-benzyl-3-((2S,3R,8S,9R,E)-3-hydroxy-9-((4-methoxybenzyl)oxy)-8-(methoxymethoxy)-2-methyltetradec-4-enoyl)oxazolidin-2-one

There total 16 articles about (S)-4-benzyl-3-((2S,3R,8S,9R,E)-3-hydroxy-9-((4-methoxybenzyl)oxy)-8-(methoxymethoxy)-2-methyltetradec-4-enoyl)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: 58.0%

: 1609652-03-0
C₂₉H₄₂O₆

: (S)-1-(4-benzyl-2-oxazolidin-3-yl)propan-1-one

: 1609652-04-1
(S)-4-benzyl-3-((2S,3R,5R,8S,9R)-5-(benzyloxy)-3-hydroxy-9-((4-methoxybenzyl)oxy)-8-(methoxymethoxy)-2-methyltetradecanoyl)oxazolidin-2-one

: 1609652-05-2
(S)-4-benzyl-3-((2S,3R,8S,9R,E)-3-hydroxy-9-((4-methoxybenzyl)oxy)-8-(methoxymethoxy)-2-methyltetradec-4-enoyl)oxazolidin-2-one

Guidance literature:: (S)-1-(4-benzyl-2-oxazolidin-3-yl)propan-1-one; With titanium tetrachloride; In dichloromethane; at 0 ℃; for 0.0833333h;

With N-ethyl-N,N-diisopropylamine; In dichloromethane; for 0.5h;

C₂₉H₄₂O₆; With 1-methyl-pyrrolidin-2-one; In dichloromethane; at -78 - 0 ℃; for 1h; stereoselective reaction;
DOI:10.1039/c4ob00323c

Reference yield:

: 1609651-95-7
(2S,3R)-2,3-dihydroxyhexyl 4-methylbenzenesulfonate

: 1609652-04-1
(S)-4-benzyl-3-((2S,3R,5R,8S,9R)-5-(benzyloxy)-3-hydroxy-9-((4-methoxybenzyl)oxy)-8-(methoxymethoxy)-2-methyltetradecanoyl)oxazolidin-2-one

: 1609652-05-2
(S)-4-benzyl-3-((2S,3R,8S,9R,E)-3-hydroxy-9-((4-methoxybenzyl)oxy)-8-(methoxymethoxy)-2-methyltetradec-4-enoyl)oxazolidin-2-one

Guidance literature:: Multi-step reaction with 13 steps

1.1: potassium carbonate / methanol / 2 h / 0 °C

2.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 0 °C

2.2: 0 - 20 °C

3.1: copper(I) bromide / tetrahydrofuran; diethyl ether / 0 °C

4.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 8 h / 0 - 20 °C

5.1: ozone / dichloromethane / -78 °C / Inert atmosphere

6.1: benzene / 2 h / 20 °C

7.1: diisobutylaluminium hydride / dichloromethane; toluene / 20 °C / Cooling

8.1: titanium(IV) isopropylate; D-(-)-diisopropyl tartrate / dichloromethane / 0.5 h / -20 °C / Molecular sieve

8.2: 3 h / -20 °C

9.1: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran; toluene / 2.5 h / 0 °C

10.1: pyridinium p-toluenesulfonate / dichloromethane / 0 °C

11.1: diisobutylaluminium hydride / dichloromethane; toluene / 2 h / -20 °C

12.1: Dess-Martin periodane / dichloromethane / 1 h / 0 - 20 °C

13.1: titanium tetrachloride / dichloromethane / 0.08 h / 0 °C

13.2: 0.5 h

13.3: 1 h / -78 - 0 °C

With titanium(IV) isopropylate; pyridinium p-toluenesulfonate; titanium tetrachloride; sodium hydride; diisobutylaluminium hydride; potassium carbonate; D-(-)-diisopropyl tartrate; Dess-Martin periodane; ozone; N-ethyl-N,N-diisopropylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; copper(I) bromide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene; mineral oil; benzene; 6.1: |Wittig Olefination / 8.1: |Sharpless Asymmetric Epoxidation / 13.2: |Evans Aldol Reaction;
DOI:10.1039/c4ob00323c

Reference yield:

: 1609652-00-7
(3R,6S,7R)-7-((4-methoxybenzyl)oxy)-6-(methoxymethoxy)dodecane-1,3-diol

: 1609652-04-1
(S)-4-benzyl-3-((2S,3R,5R,8S,9R)-5-(benzyloxy)-3-hydroxy-9-((4-methoxybenzyl)oxy)-8-(methoxymethoxy)-2-methyltetradecanoyl)oxazolidin-2-one

: 1609652-05-2
(S)-4-benzyl-3-((2S,3R,8S,9R,E)-3-hydroxy-9-((4-methoxybenzyl)oxy)-8-(methoxymethoxy)-2-methyltetradec-4-enoyl)oxazolidin-2-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: pyridinium p-toluenesulfonate / dichloromethane / 0 °C

2.1: diisobutylaluminium hydride / dichloromethane; toluene / 2 h / -20 °C

3.1: Dess-Martin periodane / dichloromethane / 1 h / 0 - 20 °C

4.1: titanium tetrachloride / dichloromethane / 0.08 h / 0 °C

4.2: 0.5 h

4.3: 1 h / -78 - 0 °C

With pyridinium p-toluenesulfonate; titanium tetrachloride; diisobutylaluminium hydride; Dess-Martin periodane; In dichloromethane; toluene; 4.2: |Evans Aldol Reaction;
DOI:10.1039/c4ob00323c