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

Base Information

• Chemical Name: [(2R,3R,4R,5S,6R)-6-(2-Azido-ethyl)-4-benzyloxy-2-benzyloxymethyl-5-methoxy-tetrahydro-pyran-3-yloxy]-tert-butyl-dimethyl-silane
• CAS No.: 511511-34-5
• Molecular Formula: C₂₉H₄₃N₃O₅Si
• Molecular Weight: 541.763

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 9 articles about [(2R,3R,4R,5S,6R)-6-(2-Azido-ethyl)-4-benzyloxy-2-benzyloxymethyl-5-methoxy-tetrahydro-pyran-3-yloxy]-tert-butyl-dimethyl-silane 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:

Methanesulfonic acid 2-[(2R,3S,4R,5R,6R)-4-benzyloxy-6-benzyloxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-tetrahydro-pyran-2-yl]-ethyl ester → [(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)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 60 ℃; for 3h;

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

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → [(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)

Guidance literature:

Multi-step reaction with 8 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

With pyridine; 1H-imidazole; lithium aluminium tetrahydride; sodium azide; 2-methyl-but-2-ene; borane; 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:

3,6-di-O-benzyl-D-glucal (145852-76-2) → [(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)

Guidance literature:

Multi-step reaction with 8 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

With pyridine; 1H-imidazole; lithium aluminium tetrahydride; sodium azide; 2-methyl-but-2-ene; borane; 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:

tert-butyldimethylsilyl chloride

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:

(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

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

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