(+)-(2R,3R,4S,5R,E)-5-Acetoxy-3-(benzyloxy)-4-hydroxy-2-methoxy-8-methyl-6-nonenoic acid 1,4-lactone

Base Information

Chemical Name:(+)-(2R,3R,4S,5R,E)-5-Acetoxy-3-(benzyloxy)-4-hydroxy-2-methoxy-8-methyl-6-nonenoic acid 1,4-lactone
CAS No.:146384-00-1
Molecular Formula:C₂₀H₂₆O₆
Molecular Weight:362.423
Hs Code.:

Synonyms:(+)-(2R,3R,4S,5R,E)-5-Acetoxy-3-(benzyloxy)-4-hydroxy-2-methoxy-8-methyl-6-nonenoic acid 1,4-lactone

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Chemical Property of (+)-(2R,3R,4S,5R,E)-5-Acetoxy-3-(benzyloxy)-4-hydroxy-2-methoxy-8-methyl-6-nonenoic acid 1,4-lactone

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Technology Process of (+)-(2R,3R,4S,5R,E)-5-Acetoxy-3-(benzyloxy)-4-hydroxy-2-methoxy-8-methyl-6-nonenoic acid 1,4-lactone

There total 5 articles about (+)-(2R,3R,4S,5R,E)-5-Acetoxy-3-(benzyloxy)-4-hydroxy-2-methoxy-8-methyl-6-nonenoic acid 1,4-lactone 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: 94.0%

: 108-24-7
acetic anhydride

: 146383-99-5
(+)-(2R,3R,4S,5R,E)-3-(Benzyloxy)-4,5-dihydroxy-2-methoxy-8-methyl-6-nonenoic acid 1,4-lactone

: 146384-00-1
(+)-(2R,3R,4S,5R,E)-5-Acetoxy-3-(benzyloxy)-4-hydroxy-2-methoxy-8-methyl-6-nonenoic acid 1,4-lactone

Guidance literature:: With pyridine; In dichloromethane; Ambient temperature;
DOI:10.1021/jo00075a017

Reference yield:

: (+/-)-(Z)-1-(Methoxymethoxy)-4-methyl-3-(tri-n-butylstannyl)-1-pentene

: 146384-00-1
(+)-(2R,3R,4S,5R,E)-5-Acetoxy-3-(benzyloxy)-4-hydroxy-2-methoxy-8-methyl-6-nonenoic acid 1,4-lactone

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) MgBr₂*OEt₂ / CH₂Cl₂ / 1.) -20 deg C, 45 min, 2.) room temp., 48 h

2: 88 percent / LiBF₄, H₂O / acetonitrile / 8 h / 75 °C

3: 94 percent / pyridine / CH₂Cl₂ / Ambient temperature

With pyridine; lithium tetrafluoroborate; water; magnesium bromide; In dichloromethane; acetonitrile;
DOI:10.1021/jo00075a017

Reference yield:

: 146383-91-7
(+)-Methyl (2R,3R)-3-(benzyloxy)-4-hydroxy-2-methoxybutanoate

: 146384-00-1
(+)-(2R,3R,4S,5R,E)-5-Acetoxy-3-(benzyloxy)-4-hydroxy-2-methoxy-8-methyl-6-nonenoic acid 1,4-lactone

Guidance literature:: Multi-step reaction with 4 steps

1: 85 percent / Dess-Martin periodinane reagent / CH₂Cl₂ / 0.58 h / Ambient temperature

2: 1.) MgBr₂*OEt₂ / CH₂Cl₂ / 1.) -20 deg C, 45 min, 2.) room temp., 48 h

3: 88 percent / LiBF₄, H₂O / acetonitrile / 8 h / 75 °C

4: 94 percent / pyridine / CH₂Cl₂ / Ambient temperature

With pyridine; lithium tetrafluoroborate; water; Dess-Martin periodane; magnesium bromide; In dichloromethane; acetonitrile;
DOI:10.1021/jo00075a017