(R)-4-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosylmethyl)-5-iodopent-1-ene

Base Information

Chemical Name:(R)-4-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosylmethyl)-5-iodopent-1-ene
CAS No.:506410-42-0
Molecular Formula:C₄₀H₄₅IO₅
Molecular Weight:732.699
Hs Code.:

Synonyms:(R)-4-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosylmethyl)-5-iodopent-1-ene

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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 (R)-4-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosylmethyl)-5-iodopent-1-ene

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Technology Process of (R)-4-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosylmethyl)-5-iodopent-1-ene

There total 5 articles about (R)-4-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosylmethyl)-5-iodopent-1-ene 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%

: 506410-41-9
(R)-2-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosylmethyl)pent-4-en-1-ol

: 506410-42-0
(R)-4-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosylmethyl)-5-iodopent-1-ene

Guidance literature:: With 1H-imidazole; iodine; triphenylphosphine; In toluene; at 20 ℃; for 0.333333h;
DOI:10.1021/jo026758d

Reference yield:

: 181489-22-5
3-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)propan-1-ol

: 506410-42-0
(R)-4-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosylmethyl)-5-iodopent-1-ene

Guidance literature:: Multi-step reaction with 5 steps

1.1: 99 percent / CrO₃; H₂SO₄ / acetone / 1.5 h / 0 - 20 °C

2.1: Et₃N; pivaloyl chloride / tetrahydrofuran / 0.25 h / -78 °C

2.2: 70 percent / BuLi / hexane; tetrahydrofuran / 0.5 h / -78 °C

3.1: 62 percent / LDA / hexane; tetrahydrofuran / 2 h / -78 - -20 °C

4.1: 94 percent / LiEt₃BH / tetrahydrofuran / 0.33 h / 0 °C

5.1: 90 percent / I₂; PPh₃; imidazole / toluene / 0.33 h / 20 °C

With 1H-imidazole; chromium(VI) oxide; sulfuric acid; iodine; pivaloyl chloride; lithium triethylborohydride; triethylamine; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; hexane; acetone; toluene; 1.1: Jones oxidation;
DOI:10.1021/jo026758d

Reference yield:

: 506410-38-4
3-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)propionic acid

: 506410-42-0
(R)-4-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosylmethyl)-5-iodopent-1-ene

Guidance literature:: Multi-step reaction with 4 steps

1.1: Et₃N; pivaloyl chloride / tetrahydrofuran / 0.25 h / -78 °C

1.2: 70 percent / BuLi / hexane; tetrahydrofuran / 0.5 h / -78 °C

2.1: 62 percent / LDA / hexane; tetrahydrofuran / 2 h / -78 - -20 °C

3.1: 94 percent / LiEt₃BH / tetrahydrofuran / 0.33 h / 0 °C

4.1: 90 percent / I₂; PPh₃; imidazole / toluene / 0.33 h / 20 °C

With 1H-imidazole; iodine; pivaloyl chloride; lithium triethylborohydride; triethylamine; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; hexane; toluene;
DOI:10.1021/jo026758d