(2R,3S,4R,6S)-4-Azido-6-[tert-butyl(dimethyl)silyl]oxy-2-(hydroxymethyl)oxan-3-ol

Base Information

• Chemical Name: (2R,3S,4R,6S)-4-Azido-6-[tert-butyl(dimethyl)silyl]oxy-2-(hydroxymethyl)oxan-3-ol
• CAS No.: 189454-43-1
• Molecular Formula: C12H25 N3 O4 Si
• Molecular Weight: 303.43
• Hs Code.: 29329990
• DSSTox Substance ID: DTXSID90443225
• Wikidata: Q82260949
• Mol file: 189454-43-1.mol

Synonyms:189454-43-1;(2R,3S,4R,6S)-4-Azido-6-[tert-butyl(dimethyl)silyl]oxy-2-(hydroxymethyl)oxan-3-ol;3-Azido-2,3-dideoxy-1-O-(tert-butyldimethylsilyl)-b-D-arabino-hexopyranose;3-AZIDO-2 3-DIDEOXY-1-O-(T-BUTYLDIMETHY&;DTXSID90443225;CHVQAMOISPQQTA-ZNSHCXBVSA-N;W-201691;3-Azido-1-O-[tert-butyl(dimethyl)silyl]-2,3-dideoxy-beta-D-arabino-hexopyranose;beta-D-arabino-Hexopyranose, 3-azido-2,3-dideoxy-1-O-[(1,1-dimethylethyl)dimethylsilyl]-

Chemical Property of (2R,3S,4R,6S)-4-Azido-6-[tert-butyl(dimethyl)silyl]oxy-2-(hydroxymethyl)oxan-3-ol

Chemical Property:

• Melting Point: 73-75 °C(lit.)
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 108.67000
• Density: g/cm³
• LogP: 1.60806
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 303.16143282
• Heavy Atom Count: 20
• Complexity: 379

Purity/Quality:

98% ^*data from raw suppliers

3-Azido-2,3-dideoxy-1-O-(tert-butyldimethylsilyl)-β-D-arabino-hexopyranose 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)[Si](C)(C)OC1CC(C(C(O1)CO)O)N=[N+]=[N-]
• Isomeric SMILES: CC(C)(C)[Si](C)(C)O[C@H]1C[C@H]([C@@H]([C@H](O1)CO)O)N=[N+]=[N-]

Technology Process of (2R,3S,4R,6S)-4-Azido-6-[tert-butyl(dimethyl)silyl]oxy-2-(hydroxymethyl)oxan-3-ol

There total 3 articles about (2R,3S,4R,6S)-4-Azido-6-[tert-butyl(dimethyl)silyl]oxy-2-(hydroxymethyl)oxan-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: 97.0%

tert-butyldimethylsilyl 3-azido-4,6-di-O-acetyl-2,3-dideoxy-β-D-arabino-hexopyranoside (189454-41-9) → 3-azido-1-O-tert-butyldimethylsilyl-2,3-dideoxy-β-D-arabinohexopyranoside (189454-43-1)

Guidance literature:

With sodium methylate; In methanol; for 1.5h; Ambient temperature;

DOI:10.1021/jm9800752

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 3-azido-1-O-tert-butyldimethylsilyl-2,3-dideoxy-β-D-arabinohexopyranoside (189454-43-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 43 percent / imidazole / CH₂Cl₂ / 1.) 0 deg C, 0.5 h, 2.) RT, 18 h

2: 97 percent / sodium methoxide / methanol / 1.5 h / Ambient temperature

With 1H-imidazole; sodium methylate; In methanol; dichloromethane;

DOI:10.1021/jm9800752

Reference yield:

4,6-di-O-acetyl-3-azido-2,3-dideoxy-D-erythro-hexopyranose → 3-azido-1-O-tert-butyldimethylsilyl-2,3-dideoxy-β-D-arabinohexopyranoside (189454-43-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 43 percent / imidazole / CH₂Cl₂ / 1.) 0 deg C, 0.5 h, 2.) RT, 18 h

2: 97 percent / sodium methoxide / methanol / 1.5 h / Ambient temperature

With 1H-imidazole; sodium methylate; In methanol; dichloromethane;

DOI:10.1021/jm9800752

upstream raw materials:

tert-butyldimethylsilyl 3-azido-4,6-di-O-acetyl-2,3-dideoxy-β-D-arabino-hexopyranoside

tert-butyldimethylsilyl chloride

Downstream raw materials:

4-O-(3-aminobenzyloxycarbonyl-2,3-dideoxy-4,6-O-ethylidene-β-D-arabino-hexopyranosyl)-4'-benzyloxycarbonyl-epipodophyllotoxin

4-O-(3-azido-2,3-dideoxy-4,6-di-O-chloroacetyl-α-D-arabino-hexopyranosyl)-4'-benzyloxycarbonyl-epipodophyllotoxin

4-O-(3-azido-2,3-dideoxy-α-D-arabino-hexopyranosyl)-4'-benzyloxycarbonyl-epipodophyllotoxin

4-O-(3-amino-2,3-dideoxy-4,6-O-ethylidene-β-D-arabino-hexopyranosyl)-epipodophyllotoxin

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