(2R,3S,4S,5R,6R)-6-[(2R,3R,4R,5S,6R)-6-(2-Azido-ethyl)-4-benzyloxy-2-benzyloxymethyl-5-methoxy-tetrahydro-pyran-3-yloxy]-3-hydroxy-4,5-dimethoxy-tetrahydro-pyran-2-carboxylic acid benzyl ester

Base Information

• Chemical Name: (2R,3S,4S,5R,6R)-6-[(2R,3R,4R,5S,6R)-6-(2-Azido-ethyl)-4-benzyloxy-2-benzyloxymethyl-5-methoxy-tetrahydro-pyran-3-yloxy]-3-hydroxy-4,5-dimethoxy-tetrahydro-pyran-2-carboxylic acid benzyl ester
• CAS No.: 511511-40-3
• Molecular Formula: C₃₈H₄₇N₃O₁₁
• Molecular Weight: 721.805

Synonyms:

Chemical Property of (2R,3S,4S,5R,6R)-6-[(2R,3R,4R,5S,6R)-6-(2-Azido-ethyl)-4-benzyloxy-2-benzyloxymethyl-5-methoxy-tetrahydro-pyran-3-yloxy]-3-hydroxy-4,5-dimethoxy-tetrahydro-pyran-2-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4S,5R,6R)-6-[(2R,3R,4R,5S,6R)-6-(2-Azido-ethyl)-4-benzyloxy-2-benzyloxymethyl-5-methoxy-tetrahydro-pyran-3-yloxy]-3-hydroxy-4,5-dimethoxy-tetrahydro-pyran-2-carboxylic acid benzyl ester

There total 17 articles about (2R,3S,4S,5R,6R)-6-[(2R,3R,4R,5S,6R)-6-(2-Azido-ethyl)-4-benzyloxy-2-benzyloxymethyl-5-methoxy-tetrahydro-pyran-3-yloxy]-3-hydroxy-4,5-dimethoxy-tetrahydro-pyran-2-carboxylic acid benzyl 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:

3,6-di-O-benzyl-D-glucal (145852-76-2) → (2R,3S,4S,5R,6R)-6-[(2R,3R,4R,5S,6R)-6-(2-Azido-ethyl)-4-benzyloxy-2-benzyloxymethyl-5-methoxy-tetrahydro-pyran-3-yloxy]-3-hydroxy-4,5-dimethoxy-tetrahydro-pyran-2-carboxylic acid benzyl ester (511511-40-3)

Guidance literature:

Multi-step reaction with 16 steps

1.1: 75 percent / imidazole / dimethylformamide / 16 h / 60 °C

2.1: 100 percent / dimethyldioxirane / acetone; CH₂Cl₂ / 0.08 h / 0 °C

3.1: 75 percent / ZnCl₂ / tetrahydrofuran; various solvent(s) / 1 h / 0 - 20 °C

4.1: 93 percent / NaH / dimethylformamide / 1 h / 0 °C

5.1: BH₃; 2-methyl-2-butene / tetrahydrofuran / 0.5 h / 0 °C

5.2: NaOH; H₂O₂ / H₂O / 1 h

6.1: 2.66 g / LiAlH₄ / tetrahydrofuran / 0.08 h / 0 °C

7.1: pyridine / CH₂Cl₂ / 16 h

8.1: 0.805 g / NaN₃ / dimethylformamide / 3 h / 60 °C

9.1: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h

10.1: 96 percent / N-iodosuccinimide; mol. sieves 4 Angstroem; TfOH / toluene; dioxane; CH₂Cl₂ / 0.5 h / -20 °C

11.1: KOtBu / methanol; dioxane / 3 h

12.1: pTsOH / dimethylformamide / 1 h

13.1: NaH / dimethylformamide / 0.5 h / 0 °C

14.1: AcOH / H₂O / 1 h / 60 °C

15.1: potassium bromide; tetrabutylammonium chloride; NaHCO₃ / NaOCl; 2,2,6,6-tetramethylpiperidin-1-oxyl / CH₂Cl₂; H₂O / 1 h / 0 °C

16.1: 0.121 mg / KHCO₃ / dimethylformamide / 2 h

With pyridine; 1H-imidazole; N-iodo-succinimide; lithium aluminium tetrahydride; sodium azide; 2-methyl-but-2-ene; trifluorormethanesulfonic acid; 4 A molecular sieve; borane; potassium tert-butylate; tetrabutyl ammonium fluoride; tetrabutyl-ammonium chloride; 3,3-dimethyldioxirane; sodium hydride; sodium hydrogencarbonate; potassium hydrogencarbonate; toluene-4-sulfonic acid; acetic acid; potassium bromide; zinc(II) chloride; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; 11.1: Zemplen deacetylation;

DOI:10.1002/1099-0690(200212)2002:23<3954::AID-EJOC3954>3.0.CO;2-2

Reference yield:

ethyl 2,4,6-tri-O-acetyl-3-O-methyl-1-thio-α/β-L-iodopyranose → (2R,3S,4S,5R,6R)-6-[(2R,3R,4R,5S,6R)-6-(2-Azido-ethyl)-4-benzyloxy-2-benzyloxymethyl-5-methoxy-tetrahydro-pyran-3-yloxy]-3-hydroxy-4,5-dimethoxy-tetrahydro-pyran-2-carboxylic acid benzyl ester (511511-40-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 96 percent / N-iodosuccinimide; mol. sieves 4 Angstroem; TfOH / toluene; dioxane; CH₂Cl₂ / 0.5 h / -20 °C

2: KOtBu / methanol; dioxane / 3 h

3: pTsOH / dimethylformamide / 1 h

4: NaH / dimethylformamide / 0.5 h / 0 °C

5: AcOH / H₂O / 1 h / 60 °C

6: potassium bromide; tetrabutylammonium chloride; NaHCO₃ / NaOCl; 2,2,6,6-tetramethylpiperidin-1-oxyl / CH₂Cl₂; H₂O / 1 h / 0 °C

7: 0.121 mg / KHCO₃ / dimethylformamide / 2 h

With N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; potassium tert-butylate; tetrabutyl-ammonium chloride; sodium hydride; sodium hydrogencarbonate; potassium hydrogencarbonate; toluene-4-sulfonic acid; acetic acid; potassium bromide; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; In 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; 2: Zemplen deacetylation;

DOI:10.1002/1099-0690(200212)2002:23<3954::AID-EJOC3954>3.0.CO;2-2

Reference yield:

1,5-anhydro-4-O-tert-butyldimethylsilyl-2-deoxy-3,6-di-O-benzyl-D-arabino-hex-1-enitol (253683-41-9) → (2R,3S,4S,5R,6R)-6-[(2R,3R,4R,5S,6R)-6-(2-Azido-ethyl)-4-benzyloxy-2-benzyloxymethyl-5-methoxy-tetrahydro-pyran-3-yloxy]-3-hydroxy-4,5-dimethoxy-tetrahydro-pyran-2-carboxylic acid benzyl ester (511511-40-3)

Guidance literature:

Multi-step reaction with 15 steps

1.1: 100 percent / dimethyldioxirane / acetone; CH₂Cl₂ / 0.08 h / 0 °C

2.1: 75 percent / ZnCl₂ / tetrahydrofuran; various solvent(s) / 1 h / 0 - 20 °C

3.1: 93 percent / NaH / dimethylformamide / 1 h / 0 °C

4.1: BH₃; 2-methyl-2-butene / tetrahydrofuran / 0.5 h / 0 °C

4.2: NaOH; H₂O₂ / H₂O / 1 h

5.1: 2.66 g / LiAlH₄ / tetrahydrofuran / 0.08 h / 0 °C

6.1: pyridine / CH₂Cl₂ / 16 h

7.1: 0.805 g / NaN₃ / dimethylformamide / 3 h / 60 °C

8.1: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h

9.1: 96 percent / N-iodosuccinimide; mol. sieves 4 Angstroem; TfOH / toluene; dioxane; CH₂Cl₂ / 0.5 h / -20 °C

10.1: KOtBu / methanol; dioxane / 3 h

11.1: pTsOH / dimethylformamide / 1 h

12.1: NaH / dimethylformamide / 0.5 h / 0 °C

13.1: AcOH / H₂O / 1 h / 60 °C

14.1: potassium bromide; tetrabutylammonium chloride; NaHCO₃ / NaOCl; 2,2,6,6-tetramethylpiperidin-1-oxyl / CH₂Cl₂; H₂O / 1 h / 0 °C

15.1: 0.121 mg / KHCO₃ / dimethylformamide / 2 h

With pyridine; N-iodo-succinimide; lithium aluminium tetrahydride; sodium azide; 2-methyl-but-2-ene; trifluorormethanesulfonic acid; 4 A molecular sieve; borane; potassium tert-butylate; tetrabutyl ammonium fluoride; tetrabutyl-ammonium chloride; 3,3-dimethyldioxirane; sodium hydride; sodium hydrogencarbonate; potassium hydrogencarbonate; toluene-4-sulfonic acid; acetic acid; potassium bromide; zinc(II) chloride; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; 10.1: Zemplen deacetylation;

DOI:10.1002/1099-0690(200212)2002:23<3954::AID-EJOC3954>3.0.CO;2-2

upstream raw materials:

benzyl bromide

3,6-di-O-benzyl-D-glucal

1,5-anhydro-4-O-tert-butyldimethylsilyl-2-deoxy-3,6-di-O-benzyl-D-arabino-hex-1-enitol

(2R,3R,4S,5S,6R)-6-(2-Azido-ethyl)-4-benzyloxy-2-benzyloxymethyl-5-methoxy-tetrahydro-pyran-3-ol

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