(1R,2R,3R,4R,5S)-2,3,4-Tris-benzyloxy-1-benzyloxymethyl-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-cyclopentanol

Base Information

Chemical Name:(1R,2R,3R,4R,5S)-2,3,4-Tris-benzyloxy-1-benzyloxymethyl-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-cyclopentanol
CAS No.:688317-64-8
Molecular Formula:C₄₀H₄₆O₈
Molecular Weight:654.8
Hs Code.:

Synonyms:(1R,2R,3R,4R,5S)-2,3,4-Tris-benzyloxy-1-benzyloxymethyl-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-cyclopentanol

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Chemical Property of (1R,2R,3R,4R,5S)-2,3,4-Tris-benzyloxy-1-benzyloxymethyl-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-cyclopentanol

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Technology Process of (1R,2R,3R,4R,5S)-2,3,4-Tris-benzyloxy-1-benzyloxymethyl-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-cyclopentanol

There total 10 articles about (1R,2R,3R,4R,5S)-2,3,4-Tris-benzyloxy-1-benzyloxymethyl-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-cyclopentanol 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: 63.0%

: 156925-79-0
[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl trifluoromethanesulfonate

: 205672-17-9
(1S,2S,3S,4R,5R)-3,4,5-Tris-benzyloxy-1-benzyloxymethyl-cyclopentane-1,2-diol

: 688317-64-8
(1R,2R,3R,4R,5S)-2,3,4-Tris-benzyloxy-1-benzyloxymethyl-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-cyclopentanol

Guidance literature:: With n-butyllithium; In tetrahydrofuran; at -78 - 0 ℃; for 6h;
DOI:10.1016/j.tetlet.2004.02.020

Reference yield:

: 100-39-0
benzyl bromide

: 688317-64-8
(1R,2R,3R,4R,5S)-2,3,4-Tris-benzyloxy-1-benzyloxymethyl-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-cyclopentanol

Guidance literature:: Multi-step reaction with 9 steps

1: 90 percent / NaH / dimethylformamide / 4 h / 0 - 20 °C

2: 91 percent / aq. H₂SO₄ / methanol / 6 h / 20 °C

3: 100 percent / Et₃N / CH₂Cl₂ / 4 h / 20 °C

4: 70 percent / sodium iodide / butan-2-one / 6 h / Heating

5: 81 percent / Grubbs' second generation catalyst / benzene / 6 h / Heating

6: 80 percent / osmium tetroxide; N-methylmorpholine N-oxide / acetone; H₂O / 12 h / 20 °C

7: 95 percent / NaH / dimethylformamide / 6 h / 0 - 20 °C

8: 80 percent / aq. acetic acid / 4 h / 60 °C

9: 63 percent / n-BuLi / tetrahydrofuran / 6 h / -78 - 0 °C

With osmium(VIII) oxide; n-butyllithium; sulfuric acid; sodium hydride; acetic acid; 4-methylmorpholine N-oxide; triethylamine; sodium iodide; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; butanone; benzene; 5: ring closing metathesis;
DOI:10.1016/j.tetlet.2004.02.020

Reference yield:

: 91738-34-0
2-C-(hydroxymethyl)-2,3:5,6-di-O-isopropylidene-α-D-mannofuranose

: 688317-64-8
(1R,2R,3R,4R,5S)-2,3,4-Tris-benzyloxy-1-benzyloxymethyl-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-cyclopentanol

Guidance literature:: Multi-step reaction with 10 steps

1: 83 percent / NaNH₂ / tetrahydrofuran; diethyl ether / 10 h / 0 - 20 °C

2: 90 percent / NaH / dimethylformamide / 4 h / 0 - 20 °C

3: 91 percent / aq. H₂SO₄ / methanol / 6 h / 20 °C

4: 100 percent / Et₃N / CH₂Cl₂ / 4 h / 20 °C

5: 70 percent / sodium iodide / butan-2-one / 6 h / Heating

6: 81 percent / Grubbs' second generation catalyst / benzene / 6 h / Heating

7: 80 percent / osmium tetroxide; N-methylmorpholine N-oxide / acetone; H₂O / 12 h / 20 °C

8: 95 percent / NaH / dimethylformamide / 6 h / 0 - 20 °C

9: 80 percent / aq. acetic acid / 4 h / 60 °C

10: 63 percent / n-BuLi / tetrahydrofuran / 6 h / -78 - 0 °C

With osmium(VIII) oxide; n-butyllithium; sulfuric acid; sodium hydride; sodium amide; acetic acid; 4-methylmorpholine N-oxide; triethylamine; sodium iodide; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone; butanone; benzene; 1: Wittig olefination / 6: ring closing metathesis;
DOI:10.1016/j.tetlet.2004.02.020