(4R,5R,6R)-5,6-Bis-benzyloxy-6-((2S,5R)-5-benzyloxymethyl-tetrahydro-furan-2-yl)-4-methyl-hexan-2-one

Base Information

Chemical Name:(4R,5R,6R)-5,6-Bis-benzyloxy-6-((2S,5R)-5-benzyloxymethyl-tetrahydro-furan-2-yl)-4-methyl-hexan-2-one
CAS No.:794517-39-8
Molecular Formula:C₃₃H₄₀O₅
Molecular Weight:516.678
Hs Code.:

Synonyms:(4R,5R,6R)-5,6-Bis-benzyloxy-6-((2S,5R)-5-benzyloxymethyl-tetrahydro-furan-2-yl)-4-methyl-hexan-2-one

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Chemical Property of (4R,5R,6R)-5,6-Bis-benzyloxy-6-((2S,5R)-5-benzyloxymethyl-tetrahydro-furan-2-yl)-4-methyl-hexan-2-one

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Technology Process of (4R,5R,6R)-5,6-Bis-benzyloxy-6-((2S,5R)-5-benzyloxymethyl-tetrahydro-furan-2-yl)-4-methyl-hexan-2-one

There total 13 articles about (4R,5R,6R)-5,6-Bis-benzyloxy-6-((2S,5R)-5-benzyloxymethyl-tetrahydro-furan-2-yl)-4-methyl-hexan-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: 95.0%

: 794517-41-2
(4R,5R,6R)-5,6-Bis-benzyloxy-6-((2S,5R)-5-benzyloxymethyl-tetrahydro-furan-2-yl)-4-methyl-hexan-2-ol

: 794517-39-8
(4R,5R,6R)-5,6-Bis-benzyloxy-6-((2S,5R)-5-benzyloxymethyl-tetrahydro-furan-2-yl)-4-methyl-hexan-2-one

Guidance literature:: With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 0.5h;
DOI:10.1016/j.tetlet.2004.08.143

Reference yield:

: 100-39-0
benzyl bromide

: 794517-39-8
(4R,5R,6R)-5,6-Bis-benzyloxy-6-((2S,5R)-5-benzyloxymethyl-tetrahydro-furan-2-yl)-4-methyl-hexan-2-one

Guidance literature:: Multi-step reaction with 12 steps

1: 94 percent / NaH / dimethylformamide / 3 h / 20 °C

2: 86 percent / Amberlyst IR 120 / 9 h / Heating

3: 92 percent / IBX / dimethylsulfoxide / 3 h / 20 °C

4: 78 percent / tetrahydrofuran; diethyl ether / 4 h / 20 °C

5: 92 percent / H₂ / Pd-C / methanol / 0.33 h / 20 °C

6: 76 percent / AcOH / 4 h / 80 °C

7: 86 percent / tetrahydrofuran; diethyl ether / 4 h / 20 °C

8: 93 percent / NaH / dimethylformamide / 3 h / 20 °C

9: 90 percent / 9-BBN; NaOH; H₂O₂ / 5 h / 20 °C

10: 96 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 20 °C

11: 87 percent / diethyl ether / 2 h / 20 °C

12: 95 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 20 °C

With sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; Amberlyst IR 120; hydrogen; dihydrogen peroxide; sodium hydride; Dess-Martin periodane; acetic acid; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; 4: Wittig reaction / 7: Wittig reaction / 11: Grignard reaction;
DOI:10.1016/j.tetlet.2004.08.143

Reference yield:

: 209849-12-7
(1S)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)pent-4-en-1-ol

: 794517-39-8
(4R,5R,6R)-5,6-Bis-benzyloxy-6-((2S,5R)-5-benzyloxymethyl-tetrahydro-furan-2-yl)-4-methyl-hexan-2-one

Guidance literature:: Multi-step reaction with 13 steps

1.1: HgCl₂ / H₂O / 1 h / 20 °C

1.2: O₂; NaBH₄ / dimethylformamide / 4 h / 20 °C

2.1: 94 percent / NaH / dimethylformamide / 3 h / 20 °C

3.1: 86 percent / Amberlyst IR 120 / 9 h / Heating

4.1: 92 percent / IBX / dimethylsulfoxide / 3 h / 20 °C

5.1: 78 percent / tetrahydrofuran; diethyl ether / 4 h / 20 °C

6.1: 92 percent / H₂ / Pd-C / methanol / 0.33 h / 20 °C

7.1: 76 percent / AcOH / 4 h / 80 °C

8.1: 86 percent / tetrahydrofuran; diethyl ether / 4 h / 20 °C

9.1: 93 percent / NaH / dimethylformamide / 3 h / 20 °C

10.1: 90 percent / 9-BBN; NaOH; H₂O₂ / 5 h / 20 °C

11.1: 96 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 20 °C

12.1: 87 percent / diethyl ether / 2 h / 20 °C

13.1: 95 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 20 °C

With sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; Amberlyst IR 120; hydrogen; dihydrogen peroxide; sodium hydride; Dess-Martin periodane; acetic acid; mercury dichloride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; 5.1: Wittig reaction / 8.1: Wittig reaction / 12.1: Grignard reaction;
DOI:10.1016/j.tetlet.2004.08.143