(Z)-4-[(2S,3S)-2-((1S,2R)-2,4-Bis-benzyloxy-1-methyl-butyl)-5-methoxy-tetrahydro-furan-3-yl]-3-methyl-but-3-en-2-one

Base Information

Chemical Name:(Z)-4-[(2S,3S)-2-((1S,2R)-2,4-Bis-benzyloxy-1-methyl-butyl)-5-methoxy-tetrahydro-furan-3-yl]-3-methyl-but-3-en-2-one
CAS No.:81114-57-0
Molecular Formula:C₂₉H₃₈O₅
Molecular Weight:466.618
Hs Code.:

Synonyms:(Z)-4-[(2S,3S)-2-((1S,2R)-2,4-Bis-benzyloxy-1-methyl-butyl)-5-methoxy-tetrahydro-furan-3-yl]-3-methyl-but-3-en-2-one

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Chemical Property of (Z)-4-[(2S,3S)-2-((1S,2R)-2,4-Bis-benzyloxy-1-methyl-butyl)-5-methoxy-tetrahydro-furan-3-yl]-3-methyl-but-3-en-2-one

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Technology Process of (Z)-4-[(2S,3S)-2-((1S,2R)-2,4-Bis-benzyloxy-1-methyl-butyl)-5-methoxy-tetrahydro-furan-3-yl]-3-methyl-but-3-en-2-one

There total 15 articles about (Z)-4-[(2S,3S)-2-((1S,2R)-2,4-Bis-benzyloxy-1-methyl-butyl)-5-methoxy-tetrahydro-furan-3-yl]-3-methyl-but-3-en-2-one 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: 90.0%

: 26487-92-3
3-(triphenylphosphoranylidene)butan-2-one

: 81123-00-4
(2R,3R)-2-((1S,2R)-2,4-Bis-benzyloxy-1-methyl-butyl)-5-methoxy-tetrahydro-furan-3-carbaldehyde

: 81114-57-0
(Z)-4-[(2S,3S)-2-((1S,2R)-2,4-Bis-benzyloxy-1-methyl-butyl)-5-methoxy-tetrahydro-furan-3-yl]-3-methyl-but-3-en-2-one

Guidance literature:: In toluene; at 60 ℃; for 90h;
DOI:10.1016/S0040-4039(01)82047-5

Reference yield:

: 100-39-0
benzyl bromide

: 81114-57-0
(Z)-4-[(2S,3S)-2-((1S,2R)-2,4-Bis-benzyloxy-1-methyl-butyl)-5-methoxy-tetrahydro-furan-3-yl]-3-methyl-but-3-en-2-one

Guidance literature:: Multi-step reaction with 11 steps

1: NaH / dimethylformamide / 1 h / 20 °C

2: H₂O, H₂SO₄ / 2-methyl-propan-2-ol / 50 °C

3: toluene / 18 h / 50 °C

4: TsOH / dimethylformamide / 1 h / 20 °C

5: BuLi / 2.5 h / -78 °C

6: BF₃ - Et₂O / 18 h / 20 °C

7: DIBAL / toluene / 0.5 h / -78 °C

8: Amberlyst 15 (H type) / 2 h / 20 °C

9: NaH / dimethylformamide / 4 h / 20 °C

10: 85 percent / CdCO₃, HgCl₂ / acetone; H₂O / 1 h / 20 °C

11: 90 percent / toluene / 90 h / 60 °C

With n-butyllithium; cadmium(II) carbonate; Amberlyst 15 (H type); sulfuric acid; boron trifluoride diethyl etherate; water; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; mercury dichloride; In water; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol;
DOI:10.1016/S0040-4039(01)82047-5

Reference yield:

: 78785-21-4
3,5-Didesoxy-1,2-O-isopropyliden-3-C-methyl-α-D-xylo-hexofuranose

: 81114-57-0
(Z)-4-[(2S,3S)-2-((1S,2R)-2,4-Bis-benzyloxy-1-methyl-butyl)-5-methoxy-tetrahydro-furan-3-yl]-3-methyl-but-3-en-2-one

Guidance literature:: Multi-step reaction with 11 steps

1: NaH / dimethylformamide / 1 h / 20 °C

2: H₂O, H₂SO₄ / 2-methyl-propan-2-ol / 50 °C

3: toluene / 18 h / 50 °C

4: TsOH / dimethylformamide / 1 h / 20 °C

5: BuLi / 2.5 h / -78 °C

6: BF₃ - Et₂O / 18 h / 20 °C

7: DIBAL / toluene / 0.5 h / -78 °C

8: Amberlyst 15 (H type) / 2 h / 20 °C

9: NaH / dimethylformamide / 4 h / 20 °C

10: 85 percent / CdCO₃, HgCl₂ / acetone; H₂O / 1 h / 20 °C

11: 90 percent / toluene / 90 h / 60 °C

With n-butyllithium; cadmium(II) carbonate; Amberlyst 15 (H type); sulfuric acid; boron trifluoride diethyl etherate; water; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; mercury dichloride; In water; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol;
DOI:10.1016/S0040-4039(01)82047-5