(3S,4S,5S)-(E)-8-benzyloxymethoxy-4-hydroxy-3,5-dimethyloct-6-enoic acid lactone

Base Information

Chemical Name:(3S,4S,5S)-(E)-8-benzyloxymethoxy-4-hydroxy-3,5-dimethyloct-6-enoic acid lactone
CAS No.:141858-92-6
Molecular Formula:C₁₈H₂₄O₄
Molecular Weight:304.386
Hs Code.:

Synonyms:(3S,4S,5S)-(E)-8-benzyloxymethoxy-4-hydroxy-3,5-dimethyloct-6-enoic acid lactone

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (3S,4S,5S)-(E)-8-benzyloxymethoxy-4-hydroxy-3,5-dimethyloct-6-enoic acid lactone

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Technology Process of (3S,4S,5S)-(E)-8-benzyloxymethoxy-4-hydroxy-3,5-dimethyloct-6-enoic acid lactone

There total 15 articles about (3S,4S,5S)-(E)-8-benzyloxymethoxy-4-hydroxy-3,5-dimethyloct-6-enoic acid 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: 81.0%

: 3587-60-8
Benzyloxymethyl chloride

: 141858-91-5
(3S,4S,5S)-(E)-4,8-dihydroxy-3,5-dimethyloct-6-enoic acid lactone

: 141858-92-6
(3S,4S,5S)-(E)-8-benzyloxymethoxy-4-hydroxy-3,5-dimethyloct-6-enoic acid lactone

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In dichloromethane; for 12h; Ambient temperature;
DOI:10.3987/COM-91-S80

Reference yield: 26.0%

: 133732-91-9
tert-butyldimethylsilyl triflate

: 141858-93-7
N-<(3S,4S,5S)-(E)-8-benzyloxymethoxy-4-hydroxy-3,5-dimethyloct-6-enoyl>pyrrolidine

: 141858-92-6
(3S,4S,5S)-(E)-8-benzyloxymethoxy-4-hydroxy-3,5-dimethyloct-6-enoic acid lactone

: 141858-94-8
N-<(3S,4S,5S)-(E)-8-benzyloxymethoxy-4-tert-butyldimethylsilyloxy-3,5-dimethyloct-6-enoyl>pyrrolidine

Guidance literature:: With 2,6-dimethylpyridine; for 0.166667h; Ambient temperature;
DOI:10.3987/COM-91-S80

Reference yield:

: 111149-31-6
(3R,4S)-(E)-7-benzyloxy-4-methyl-1-trimethylsilylhept-5-en-1-yn-3-ol

: 141858-92-6
(3S,4S,5S)-(E)-8-benzyloxymethoxy-4-hydroxy-3,5-dimethyloct-6-enoic acid lactone

Guidance literature:: Multi-step reaction with 8 steps

1: 96 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.13 h / Ambient temperature

2: 1.) n-BuLi / 1.) THF, -30 deg C, 15 min, 2.) THF, -30 deg C

3: H₂ / Lindlar catalyst / ethyl acetate / 16 h / 760 Torr

4: benzene / 16.5 h / Heating

5: 65 percent / diethyl ether / 0.17 h / 0 °C

6: 95 percent / NaI, trimethylsilyl chloride / CH₂Cl₂; acetonitrile / 4 h / Ambient temperature

7: 72 percent / NaHCO₃ / tetrahydrofuran; H₂O / 96 h / Ambient temperature

8: 81 percent / (i-Pr)2NEt / CH₂Cl₂ / 12 h / Ambient temperature

With n-butyllithium; chloro-trimethyl-silane; tetrabutyl ammonium fluoride; hydrogen; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; sodium iodide; Lindlar's catalyst; In tetrahydrofuran; diethyl ether; dichloromethane; water; ethyl acetate; acetonitrile; benzene;
DOI:10.3987/COM-91-S80