(+) methyl (5S,6S)-6-benzyloxy-5-hydroxy-3-oxodecanoate

Base Information

Chemical Name:(+) methyl (5S,6S)-6-benzyloxy-5-hydroxy-3-oxodecanoate
CAS No.:139068-40-9
Molecular Formula:C₁₈H₂₆O₅
Molecular Weight:322.401
Hs Code.:

Synonyms:(+) methyl (5S,6S)-6-benzyloxy-5-hydroxy-3-oxodecanoate

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Chemical Property of (+) methyl (5S,6S)-6-benzyloxy-5-hydroxy-3-oxodecanoate

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Technology Process of (+) methyl (5S,6S)-6-benzyloxy-5-hydroxy-3-oxodecanoate

There total 27 articles about (+) methyl (5S,6S)-6-benzyloxy-5-hydroxy-3-oxodecanoate 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: 66.0%

: 81114-98-9
Chan's diene

: 66832-04-0,106225-83-6,139068-40-9
methyl 6-benzyloxy-5-hydroxy-3-oxodecanoate

Guidance literature:: With titanium tetrachloride; In dichloromethane; at -80 ℃;
DOI:10.1039/P19920000693

Reference yield:

: 74590-73-1,81114-98-9,67609-52-3
1,3-bis(trimethylsiloxy)-1-methoxybuta-1,3-diene

: 87678-65-7
(S)-(-)-2-benzyloxyhexanal

: C₁₈H₂₆O₅

: C₁₈H₂₆O₅

: 139068-40-9
(+) methyl (5S,6S)-6-benzyloxy-5-hydroxy-3-oxodecanoate

Guidance literature:: (S)-(-)-2-benzyloxyhexanal; With titanium(IV) isopropylate; (S)-[1,1']-binaphthalenyl-2,2'-diol; lithium chloride; In tetrahydrofuran; at 20 - 25 ℃; for 0.5h; Inert atmosphere;

1,3-bis(trimethylsiloxy)-1-methoxybuta-1,3-diene; In tetrahydrofuran; at 20 - 25 ℃; for 14h; Inert atmosphere;

With pyridinium p-toluenesulfonate; In tetrahydrofuran; methanol; at 20 - 25 ℃; for 2h; Overall yield = 31 percent; Overall yield = 51 mg; Inert atmosphere;
DOI:10.3390/molecules25020394

Reference yield:

: 87604-60-2
(S)-(+)-2-benzyloxyhexan-1-ol

: C₁₈H₂₆O₅

: C₁₈H₂₆O₅

: 139068-40-9
(+) methyl (5S,6S)-6-benzyloxy-5-hydroxy-3-oxodecanoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium bromide; sodium hypochlorite; sodium hydrogencarbonate; sodium carbonate / dichloromethane; water / 1 h / 0 - 25 °C / Inert atmosphere

2.1: titanium(IV) isopropylate; (S)-[1,1']-binaphthalenyl-2,2'-diol; lithium chloride / tetrahydrofuran / 0.5 h / 20 - 25 °C / Inert atmosphere

2.2: 14 h / 20 - 25 °C / Inert atmosphere

2.3: 2 h / 20 - 25 °C / Inert atmosphere

With titanium(IV) isopropylate; sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; (S)-[1,1']-binaphthalenyl-2,2'-diol; sodium hydrogencarbonate; sodium carbonate; lithium chloride; potassium bromide; In tetrahydrofuran; dichloromethane; water; 2.1: |Mukaiyama Aldol Addition / 2.2: |Mukaiyama Aldol Addition;
DOI:10.3390/molecules25020394