4-Oxo-pentanoic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-2-pent-4-enyloxy-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-3-yl ester

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Chemical Name:4-Oxo-pentanoic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-2-pent-4-enyloxy-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-3-yl ester
CAS No.:915150-35-5
Molecular Formula:C₃₉H₅₈O₈Si
Molecular Weight:682.97
Hs Code.:

Synonyms:4-Oxo-pentanoic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-2-pent-4-enyloxy-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-3-yl ester

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Chemical Property of 4-Oxo-pentanoic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-2-pent-4-enyloxy-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-3-yl ester

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Technology Process of 4-Oxo-pentanoic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-2-pent-4-enyloxy-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-3-yl ester

There total 9 articles about 4-Oxo-pentanoic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-2-pent-4-enyloxy-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-3-yl ester 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: 96.0%

: (2S,3S,4R,5R,6R)-4,5-Bis-benzyloxy-2-pent-4-enyloxy-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-3-ol

: 123-76-2
levulinic acid

: 915150-35-5
4-Oxo-pentanoic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-2-pent-4-enyloxy-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-3-yl ester

Guidance literature:: With dmap; diisopropyl-carbodiimide; In dichloromethane; at 0 - 20 ℃;
DOI:10.1021/jo061233x

Reference yield:

: 14218-11-2,14218-30-5,61198-88-7,108438-33-1,108836-02-8,114682-36-9,127305-34-4,151377-77-4
2,3,4,6-Tetra-O-benzoyl-α-D-mannopyranosyl bromide

: 915150-35-5
4-Oxo-pentanoic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-2-pent-4-enyloxy-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 2,6-lutidine / CH₂Cl₂ / 72 h / 20 °C

2: 2.40 g / NaOMe / methanol / 24 h / 24 °C

3: 66 percent / imidazole / dimethylformamide / 0 - 20 °C

4: 95 percent / imidazole; NaH / dimethylformamide / 0 - 20 °C

5: acetic acid / tetrahydrofuran / 4 h / 20 °C

6: 2.53 g / DBU / CH₂Cl₂ / 0.25 h / 0 °C

7: 88 percent / TMSOTf / CH₂Cl₂ / 0 °C

8: 88 percent / NaOMe / CH₂Cl₂; methanol / 20 °C

9: 96 percent / 4-(dimethylamino)pyridine; N,N'-diisopropylcarbodiimide / CH₂Cl₂ / 0 - 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; dmap; trimethylsilyl trifluoromethanesulfonate; sodium methylate; sodium hydride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; diisopropyl-carbodiimide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo061233x

Reference yield:

: 883878-96-4
3,4-di-O-benzyl-1,2-O-(α-methoxybenzylidene)-6-O-(triisopropylsilyl)-β-D-mannopyranose

: 915150-35-5
4-Oxo-pentanoic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-2-pent-4-enyloxy-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 5 steps

1: acetic acid / tetrahydrofuran / 4 h / 20 °C

2: 2.53 g / DBU / CH₂Cl₂ / 0.25 h / 0 °C

3: 88 percent / TMSOTf / CH₂Cl₂ / 0 °C

4: 88 percent / NaOMe / CH₂Cl₂; methanol / 20 °C

5: 96 percent / 4-(dimethylamino)pyridine; N,N'-diisopropylcarbodiimide / CH₂Cl₂ / 0 - 20 °C

With dmap; trimethylsilyl trifluoromethanesulfonate; sodium methylate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; diisopropyl-carbodiimide; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/jo061233x