3,4-di-O-benzyl-6-O-(tert-butyldimethylsilyl)-2-deoxy-α-D-lyxo-hexopyranosyl azide

Base Information

• Chemical Name: 3,4-di-O-benzyl-6-O-(tert-butyldimethylsilyl)-2-deoxy-α-D-lyxo-hexopyranosyl azide
• CAS No.: 683788-66-1
• Molecular Formula: C₂₆H₃₇N₃O₄Si
• Molecular Weight: 483.683
• Mol file: 683788-66-1.mol

Synonyms:3,4-di-O-benzyl-6-O-(tert-butyldimethylsilyl)-2-deoxy-α-D-lyxo-hexopyranosyl azide

Chemical Property of 3,4-di-O-benzyl-6-O-(tert-butyldimethylsilyl)-2-deoxy-α-D-lyxo-hexopyranosyl azide

Chemical Property:

Purity/Quality:

Safty Information:

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• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,4-di-O-benzyl-6-O-(tert-butyldimethylsilyl)-2-deoxy-α-D-lyxo-hexopyranosyl azide

There total 1 articles about 3,4-di-O-benzyl-6-O-(tert-butyldimethylsilyl)-2-deoxy-α-D-lyxo-hexopyranosyl azide 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: 55.0%

(2R,3R,4R)-((3,4-bis(benzyloxy)-3,4-dihydro-2H-pyran-2-yl)-methoxy)(tert-butyl)dimethylsilane (136656-50-3) → 3,4-di-O-benzyl-6-O-(tert-butyldimethylsilyl)-2-deoxy-α-D-lyxo-hexopyranosyl azide (683788-66-1)

Guidance literature:

With trimethylsilylazide; Salpetersaeuretrimethylsilylester; In acetonitrile; for 5h; pH=2.5;

DOI:10.1021/jo0354948

Reference yield:

3,4-di-O-benzyl-6-O-(tert-butyldimethylsilyl)-2-deoxy-α-D-lyxo-hexopyranosyl azide (683788-66-1) → (4R,5R,6R)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-2-ylamine

Guidance literature:

With water; triphenylphosphine; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1021/jo0354948

Reference yield:

3,4-di-O-benzyl-6-O-(tert-butyldimethylsilyl)-2-deoxy-α-D-lyxo-hexopyranosyl azide (683788-66-1) → (2S,3R,4R,6R)-6-Acetylamino-3,4-bis-benzyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester

Guidance literature:

Multi-step reaction with 5 steps

1: triphenylphosphine; water / tetrahydrofuran / 1 h / 20 °C

2: 217 mg / pyridine / 4 h / 20 °C

3: 92 percent / TBAF / tetrahydrofuran / 0 - 20 °C

4: TEMPO; NaOCl; KBr / NaHCO₃ / acetone; H₂O / 2 h / 0 °C

5: 61 mg / tetrahydrofuran / 0.5 h / 0 °C

With pyridine; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; tetrabutyl ammonium fluoride; water; triphenylphosphine; potassium bromide; sodium hydrogencarbonate; In tetrahydrofuran; water; acetone;

DOI:10.1021/jo0354948

upstream raw materials:

(2R,3R,4R)-((3,4-bis(benzyloxy)-3,4-dihydro-2H-pyran-2-yl)-methoxy)(tert-butyl)dimethylsilane