(E,5SR)-6-<(2RS,6SR)-6-<2-benzyloxyethyl>-5,6-dihydro-2H-pyran-2-yl>-5-hydroxy-2-methylhexa-2-enal

Base Information

• Chemical Name: (E,5SR)-6-<(2RS,6SR)-6-<2-benzyloxyethyl>-5,6-dihydro-2H-pyran-2-yl>-5-hydroxy-2-methylhexa-2-enal
• CAS No.: 140902-83-6
• Molecular Formula: C₂₁H₂₈O₄
• Molecular Weight: 344.451

Synonyms:(E,5SR)-6-<(2RS,6SR)-6-<2-benzyloxyethyl>-5,6-dihydro-2H-pyran-2-yl>-5-hydroxy-2-methylhexa-2-enal

Chemical Property of (E,5SR)-6-<(2RS,6SR)-6-<2-benzyloxyethyl>-5,6-dihydro-2H-pyran-2-yl>-5-hydroxy-2-methylhexa-2-enal

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Technology Process of (E,5SR)-6-<(2RS,6SR)-6-<2-benzyloxyethyl>-5,6-dihydro-2H-pyran-2-yl>-5-hydroxy-2-methylhexa-2-enal

There total 1 articles about (E,5SR)-6-<(2RS,6SR)-6-<2-benzyloxyethyl>-5,6-dihydro-2H-pyran-2-yl>-5-hydroxy-2-methylhexa-2-enal 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: 7.0%

(E)-trimethyl(2-methylbuta-1,3-dienyloxy)silane (54623-57-3) + (2RS,6SR)-6-benzyloxyethyl-5,6-dihydro-2-formylmethyl-2H-pyran (140902-80-3) → (E,5SR)-6-<(2RS,6SR)-6-<2-benzyloxyethyl>-5,6-dihydro-2H-pyran-2-yl>-5-hydroxy-2-methylhexa-2-enal (140902-83-6) + (E,5RS)-6-<(2RS,6SR)-6-<2-benzyloxyethyl>-5,6-dihydro-2H-pyran-2-yl>-5-hydroxy-2-methylhexa-2-enal (141041-72-7)

Guidance literature:

With boron trifluoride diethyl etherate; In diethyl ether; dichloromethane; at -78 ℃; for 2.3h;

DOI:10.1016/0040-4020(95)00547-L

Reference yield: 90.0%

trimethyl phosphonoacetate (5927-18-4) + (E,5SR)-6-<(2RS,6SR)-6-<2-benzyloxyethyl>-5,6-dihydro-2H-pyran-2-yl>-5-hydroxy-2-methylhexa-2-enal (140902-83-6) → (E,E,7SR)-methyl-8-<(2RS,6SR)-6-<2-benzyloxyethyl>-5,6-dihydro-2H-pyran-2-yl>-7-hydroxy-4-methylocta-2,4-dienoate (140902-84-7)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; at 0 - 20 ℃; for 1h;

DOI:10.1016/0040-4020(95)00547-L

Reference yield:

(E,5SR)-6-<(2RS,6SR)-6-<2-benzyloxyethyl>-5,6-dihydro-2H-pyran-2-yl>-5-hydroxy-2-methylhexa-2-enal (140902-83-6) → (E)-(R)-6-[(2S,6R)-6-(2-Benzyloxy-ethyl)-5,6-dihydro-2H-pyran-2-yl]-5-hydroxy-2-methyl-hex-2-enoic acid

Guidance literature:

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; In tert-butyl alcohol;

DOI:10.1021/jo00038a002

upstream raw materials:

(E)-trimethyl(2-methylbuta-1,3-dienyloxy)silane

(2RS,6SR)-6-benzyloxyethyl-5,6-dihydro-2-formylmethyl-2H-pyran

Downstream raw materials:

(E,E,7SR)-methyl-8-<(2RS,6SR)-6-<2-benzyloxyethyl>-5,6-dihydro-2H-pyran-2-yl>-7-hydroxy-4-methylocta-2,4-dienoate

(E)-(R)-6-[(2S,6R)-6-(2-Benzyloxy-ethyl)-5,6-dihydro-2H-pyran-2-yl]-5-(tert-butyl-dimethyl-silanyloxy)-2-methyl-hex-2-enoic acid methyl ester

(E,E,7SR)-methyl-8-<(2RS,6SR)-6-<2-benzyloxyethyl>-5,6-dihydro-2H-pyran-2-yl>-7-(tert-butyldimethylsilyloxy)-4-methylocta-2,4-dienoate

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