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

Base Information

• Chemical Name: (2R,3R,4S,5S,6R)-6-(2-Azido-ethyl)-4-benzyloxy-2-benzyloxymethyl-5-methoxy-tetrahydro-pyran-3-ol
• CAS No.: 511511-28-7
• Molecular Formula: C₂₃H₂₉N₃O₅
• Molecular Weight: 427.5

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

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

There total 9 articles about (2R,3R,4S,5S,6R)-6-(2-Azido-ethyl)-4-benzyloxy-2-benzyloxymethyl-5-methoxy-tetrahydro-pyran-3-ol 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: 99.0%

[(2R,3R,4R,5S,6R)-6-(2-Azido-ethyl)-4-benzyloxy-2-benzyloxymethyl-5-methoxy-tetrahydro-pyran-3-yloxy]-tert-butyl-dimethyl-silane (511511-34-5) → (2R,3R,4S,5S,6R)-6-(2-Azido-ethyl)-4-benzyloxy-2-benzyloxymethyl-5-methoxy-tetrahydro-pyran-3-ol (511511-28-7)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 3h;

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

Reference yield:

3,6-di-O-benzyl-D-glucal (145852-76-2) → (2R,3R,4S,5S,6R)-6-(2-Azido-ethyl)-4-benzyloxy-2-benzyloxymethyl-5-methoxy-tetrahydro-pyran-3-ol (511511-28-7)

Guidance literature:

Multi-step reaction with 9 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

With pyridine; 1H-imidazole; lithium aluminium tetrahydride; sodium azide; 2-methyl-but-2-ene; borane; tetrabutyl ammonium fluoride; 3,3-dimethyldioxirane; sodium hydride; zinc(II) chloride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetone;

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,3R,4S,5S,6R)-6-(2-Azido-ethyl)-4-benzyloxy-2-benzyloxymethyl-5-methoxy-tetrahydro-pyran-3-ol (511511-28-7)

Guidance literature:

Multi-step reaction with 8 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

With pyridine; lithium aluminium tetrahydride; sodium azide; 2-methyl-but-2-ene; borane; tetrabutyl ammonium fluoride; 3,3-dimethyldioxirane; sodium hydride; zinc(II) chloride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetone;

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

upstream raw materials:

[(2R,3R,4R,5S,6R)-6-(2-Azido-ethyl)-4-benzyloxy-2-benzyloxymethyl-5-methoxy-tetrahydro-pyran-3-yloxy]-tert-butyl-dimethyl-silane

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

((1S,3R,4R,5R,6R)-5-Benzyloxy-3-benzyloxymethyl-2,7-dioxa-bicyclo[4.1.0]hept-4-yloxy)-tert-butyl-dimethyl-silane

Downstream raw materials:

Acetic acid (2S,3R,4S,5R,6S)-5-acetoxy-6-acetoxymethyl-2-[(2R,3R,4R,5S,6R)-6-(2-azido-ethyl)-4-benzyloxy-2-benzyloxymethyl-5-methoxy-tetrahydro-pyran-3-yloxy]-4-methoxy-tetrahydro-pyran-3-yl ester

(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

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