(E)-(1R,2S,5R)-5-((2S,3S,4S,5S)-3-Benzyloxy-5-methoxy-4-methyl-tetrahydro-furan-2-yl)-1-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)-5-methoxymethoxy-2,4-dimethyl-pent-3-en-1-ol

Base Information

Chemical Name:(E)-(1R,2S,5R)-5-((2S,3S,4S,5S)-3-Benzyloxy-5-methoxy-4-methyl-tetrahydro-furan-2-yl)-1-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)-5-methoxymethoxy-2,4-dimethyl-pent-3-en-1-ol
CAS No.:147910-26-7
Molecular Formula:C₂₇H₄₁NO₇
Molecular Weight:491.625
Hs Code.:

(E)-(1R,2S,5R)-5-((2S,3S,4S,5S)-3-Benzyloxy-5-methoxy-4-methyl-tetrahydro-furan-2-yl)-1-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)-5-methoxymethoxy-2,4-dimethyl-pent-3-en-1-ol

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Chemical Property of (E)-(1R,2S,5R)-5-((2S,3S,4S,5S)-3-Benzyloxy-5-methoxy-4-methyl-tetrahydro-furan-2-yl)-1-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)-5-methoxymethoxy-2,4-dimethyl-pent-3-en-1-ol

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Technology Process of (E)-(1R,2S,5R)-5-((2S,3S,4S,5S)-3-Benzyloxy-5-methoxy-4-methyl-tetrahydro-furan-2-yl)-1-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)-5-methoxymethoxy-2,4-dimethyl-pent-3-en-1-ol

There total 14 articles about (E)-(1R,2S,5R)-5-((2S,3S,4S,5S)-3-Benzyloxy-5-methoxy-4-methyl-tetrahydro-furan-2-yl)-1-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)-5-methoxymethoxy-2,4-dimethyl-pent-3-en-1-ol 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:

: 2-{(E)-(S)-1-[(S)-((2S,3S,4S,5S)-3-Benzyloxy-5-methoxy-4-methyl-tetrahydro-furan-2-yl)-methoxymethoxy-methyl]-1-methyl-but-2-enyloxymethyl}-4,4-dimethyl-4,5-dihydro-oxazole

: 147910-26-7
(E)-(1R,2S,5R)-5-((2S,3S,4S,5S)-3-Benzyloxy-5-methoxy-4-methyl-tetrahydro-furan-2-yl)-1-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)-5-methoxymethoxy-2,4-dimethyl-pent-3-en-1-ol

Guidance literature:: With n-butyllithium; In tetrahydrofuran; at -78 ℃;
DOI:10.1016/0040-4039(96)01217-8

Reference yield:

: 2-{(E)-(S)-1-[(S)-((2S,3S,4S,5S)-3-Benzyloxy-5-methoxy-4-methyl-tetrahydro-furan-2-yl)-methoxymethoxy-methyl]-1-methyl-but-2-enyloxymethyl}-4,4-dimethyl-4,5-dihydro-oxazole

: (Z)-(1R,2S,5R)-5-((2S,3S,4S,5S)-3-Benzyloxy-5-methoxy-4-methyl-tetrahydro-furan-2-yl)-1-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)-5-methoxymethoxy-2,4-dimethyl-pent-3-en-1-ol

: 147910-26-7
(E)-(1R,2S,5R)-5-((2S,3S,4S,5S)-3-Benzyloxy-5-methoxy-4-methyl-tetrahydro-furan-2-yl)-1-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)-5-methoxymethoxy-2,4-dimethyl-pent-3-en-1-ol

Guidance literature:: With n-butyllithium; In tetrahydrofuran; at -78 ℃; Yield given. Yields of byproduct given;
DOI:10.1016/0040-4039(93)89003-9

Reference yield:

: 109958-35-2
(2R,4aR,6S,7S,8S,8aS)-8-Benzyloxy-6-methoxy-7-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

: 147910-26-7
(E)-(1R,2S,5R)-5-((2S,3S,4S,5S)-3-Benzyloxy-5-methoxy-4-methyl-tetrahydro-furan-2-yl)-1-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)-5-methoxymethoxy-2,4-dimethyl-pent-3-en-1-ol

Guidance literature:: Multi-step reaction with 11 steps

1: HCl, MeOH

2: imidazole / tetrahydrofuran

3: i-Pr₂NEt

4: 99 percent / n-Bu₄NF / tetrahydrofuran

5: (COCl)2, DMSO, NEt₃ / CH₂Cl₂

6: tetrahydrofuran / -78 °C

7: (COCl)2, DMSO, NEt₃ / CH₂Cl₂

8: tetrahydrofuran / -78 °C

9: LiAlH₄ / tetrahydrofuran / 45 °C

10: KH / 1,2-dimethoxy-ethane

11: n-BuLi / tetrahydrofuran / -78 °C

With 1H-imidazole; hydrogenchloride; methanol; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; tetrabutyl ammonium fluoride; potassium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane;
DOI:10.1016/0040-4039(93)89003-9