(E)-(2S,3R,4R,5S)-2-Benzoylamino-3-benzyloxy-4,5-dihydroxy-2-hydroxymethyl-14-oxo-icos-6-enoic acid

Base Information

• Chemical Name: (E)-(2S,3R,4R,5S)-2-Benzoylamino-3-benzyloxy-4,5-dihydroxy-2-hydroxymethyl-14-oxo-icos-6-enoic acid
• CAS No.: 500783-38-0
• Molecular Formula: C₃₅H₄₉NO₈
• Molecular Weight: 611.776

Synonyms:(E)-(2S,3R,4R,5S)-2-Benzoylamino-3-benzyloxy-4,5-dihydroxy-2-hydroxymethyl-14-oxo-icos-6-enoic acid

Chemical Property of (E)-(2S,3R,4R,5S)-2-Benzoylamino-3-benzyloxy-4,5-dihydroxy-2-hydroxymethyl-14-oxo-icos-6-enoic acid

Chemical Property:

Purity/Quality:

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Technology Process of (E)-(2S,3R,4R,5S)-2-Benzoylamino-3-benzyloxy-4,5-dihydroxy-2-hydroxymethyl-14-oxo-icos-6-enoic acid

There total 11 articles about (E)-(2S,3R,4R,5S)-2-Benzoylamino-3-benzyloxy-4,5-dihydroxy-2-hydroxymethyl-14-oxo-icos-6-enoic acid 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: 100.0%

(2'E,1'S,3S,4R,5R)-3-benzamido-4-benzyloxy-3-hydroxymethyl-5-(1'-hydroxy-10'-oxo-hexadec-2'-en-1'-yl)-2-oxo-tetrahydrofuran (400746-76-1) → (E)-(2S,3R,4R,5S)-2-Benzoylamino-3-benzyloxy-4,5-dihydroxy-2-hydroxymethyl-14-oxo-icos-6-enoic acid (500783-38-0)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1016/S0040-4020(02)01058-X

Reference yield:

(1'S,3S,4R,5S)-3-azido-4-benzyloxy-5-[2'-(tert-butyldimethylsilyloxy)-1'-[2-(trimethylsilyl)ethoxymethoxy]ethyl]-3-(tert-butyldiphenylsilyloxymethyl)-2-oxo-tetrahydrofuran (344615-51-6) → (E)-(2S,3R,4R,5S)-2-Benzoylamino-3-benzyloxy-4,5-dihydroxy-2-hydroxymethyl-14-oxo-icos-6-enoic acid (500783-38-0)

Guidance literature:

Multi-step reaction with 9 steps

1.1: H₂ / Pd/C / ethyl acetate / 3 h / 20 °C

2.1: 0.21 percent / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 1 h / 20 °C

3.1: 82 percent / H₂SO₄ / H₂O; acetone / 3 h / 20 °C

4.1: Dess-Martin periodinane / CH₂Cl₂ / 1.5 h / 20 °C

5.1: 48 mg / CrCl₂ / tetrahydrofuran / 3 h / 0 - 20 °C

6.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 2 h / 20 °C

6.2: 94 percent / Ph₃As; Cs₂CO₃; [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium / tetrahydrofuran; H₂O; dimethylformamide / 2 h / 0 - 20 °C

7.1: H₂SO₄ / acetone; H₂O / 5 h / 20 °C

8.1: 6.3 mg / HF-pyridine complex / tetrahydrofuran / 5 h / 20 °C

9.1: 100 percent / NaOH / tetrahydrofuran / 1 h / 20 °C

With chromium dichloride; dmap; sodium hydroxide; sulfuric acid; hydrogen; Dess-Martin periodane; pyridine hydrogenfluoride; triethylamine; 9-bora-bicyclo[3.3.1]nonane; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; ethyl acetate; acetone; 6.2: Suzuki-Miyaura reaction;

DOI:10.1016/S0040-4020(02)01058-X

Reference yield:

(2S,3R,4R,5S)-N,N-dimethyl-2-azido-3-benzyloxy-6-(tert-butyldimethylsilyloxy)-2-(tert-butyldiphenylsilyloxymethyl)-4-(p-methoxybenzyloxy)-5-[2-(trimethylsilyl)ethoxymethoxy]hexanoamide (344615-50-5) → (E)-(2S,3R,4R,5S)-2-Benzoylamino-3-benzyloxy-4,5-dihydroxy-2-hydroxymethyl-14-oxo-icos-6-enoic acid (500783-38-0)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; H₂O / 3 h / 20 °C

1.2: 62 percent / pyridinium p-toluenesulfonate / toluene / 24 h / 70 °C

2.1: H₂ / Pd/C / ethyl acetate / 3 h / 20 °C

3.1: 0.21 percent / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 1 h / 20 °C

4.1: 82 percent / H₂SO₄ / H₂O; acetone / 3 h / 20 °C

5.1: Dess-Martin periodinane / CH₂Cl₂ / 1.5 h / 20 °C

6.1: 48 mg / CrCl₂ / tetrahydrofuran / 3 h / 0 - 20 °C

7.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 2 h / 20 °C

7.2: 94 percent / Ph₃As; Cs₂CO₃; [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium / tetrahydrofuran; H₂O; dimethylformamide / 2 h / 0 - 20 °C

8.1: H₂SO₄ / acetone; H₂O / 5 h / 20 °C

9.1: 6.3 mg / HF-pyridine complex / tetrahydrofuran / 5 h / 20 °C

10.1: 100 percent / NaOH / tetrahydrofuran / 1 h / 20 °C

With chromium dichloride; dmap; sodium hydroxide; sulfuric acid; hydrogen; Dess-Martin periodane; pyridine hydrogenfluoride; triethylamine; 9-bora-bicyclo[3.3.1]nonane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; ethyl acetate; acetone; 7.2: Suzuki-Miyaura reaction;

DOI:10.1016/S0040-4020(02)01058-X

upstream raw materials:

(2'E,1'S,3S,4R,5R)-3-benzamido-4-benzyloxy-3-hydroxymethyl-5-(1'-hydroxy-10'-oxo-hexadec-2'-en-1'-yl)-2-oxo-tetrahydrofuran

benzoyl chloride

(1'S,3S,4R,5S)-3-azido-4-benzyloxy-5-[2'-(tert-butyldimethylsilyloxy)-1'-[2-(trimethylsilyl)ethoxymethoxy]ethyl]-3-(tert-butyldiphenylsilyloxymethyl)-2-oxo-tetrahydrofuran

(2S,3R,4R,5S)-N,N-dimethyl-2-azido-3-benzyloxy-6-(tert-butyldimethylsilyloxy)-2-(tert-butyldiphenylsilyloxymethyl)-4-(p-methoxybenzyloxy)-5-[2-(trimethylsilyl)ethoxymethoxy]hexanoamide

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