(Z)-1,6-anhydro-4-O-(tert-butyldiphenylsilyl)-3-deoxy-3-methoxyimine-2-O-(prop-2'-inyl)-β-D-arabino-hexopyranose

Base Information

• Chemical Name: (Z)-1,6-anhydro-4-O-(tert-butyldiphenylsilyl)-3-deoxy-3-methoxyimine-2-O-(prop-2'-inyl)-β-D-arabino-hexopyranose
• CAS No.: 190188-95-5
• Molecular Formula: C₂₆H₃₁NO₅Si
• Molecular Weight: 465.621
• Mol file: 190188-95-5.mol

Synonyms:(Z)-1,6-anhydro-4-O-(tert-butyldiphenylsilyl)-3-deoxy-3-methoxyimine-2-O-(prop-2'-inyl)-β-D-arabino-hexopyranose

Chemical Property of (Z)-1,6-anhydro-4-O-(tert-butyldiphenylsilyl)-3-deoxy-3-methoxyimine-2-O-(prop-2'-inyl)-β-D-arabino-hexopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-1,6-anhydro-4-O-(tert-butyldiphenylsilyl)-3-deoxy-3-methoxyimine-2-O-(prop-2'-inyl)-β-D-arabino-hexopyranose

There total 9 articles about (Z)-1,6-anhydro-4-O-(tert-butyldiphenylsilyl)-3-deoxy-3-methoxyimine-2-O-(prop-2'-inyl)-β-D-arabino-hexopyranose 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:

propargyl bromide (106-96-7) + (3Z)-1,6-anhydro-4-O-(tert-butyldiphenylsilyl)-3-deoxy-3-methoxyimine-β-D-arabino-hexopyranose (190188-88-6) → (Z)-1,6-anhydro-4-O-(tert-butyldiphenylsilyl)-3-deoxy-3-methoxyimine-2-O-(prop-2'-inyl)-β-D-arabino-hexopyranose (190188-95-5)

Guidance literature:

With sodium hydride; Yield given. Multistep reaction; 1.) THF, 0 deg C;

DOI:10.1016/S0040-4039(97)00460-7

Reference yield:

1,6-anhydro-2,3-O-isopropylidene-β-D-mannopyranose (14440-51-8) → (Z)-1,6-anhydro-4-O-(tert-butyldiphenylsilyl)-3-deoxy-3-methoxyimine-2-O-(prop-2'-inyl)-β-D-arabino-hexopyranose (190188-95-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 92 percent / imidazole / dimethylformamide

2.1: H₂O / acetone / 80 °C

3.1: 93 percent / n-Bu₂SnO; Br₂ / benzene / Heating

4.1: 89 percent / pyridine / CH₂Cl₂ / 3 h / Heating

5.1: NaH / tetrahydrofuran; various solvent(s) / 0 °C

5.2: 820 mg / tetrahydrofuran; various solvent(s) / cooling

With pyridine; 1H-imidazole; water; bromine; sodium hydride; di(n-butyl)tin oxide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetone; benzene; 1.1: Substitution / 2.1: Hydrolysis / 3.1: Oxidation / 4.1: Condensation / 5.1: Metallation / 5.2: Alkylation;

DOI:10.1021/jo000325y

Reference yield:

1,6-anhydro-4-O-(tert-butyldiphenylsilyl)-β-D-arabino-hexopyran-3-ulose (149793-78-2) → (Z)-1,6-anhydro-4-O-(tert-butyldiphenylsilyl)-3-deoxy-3-methoxyimine-2-O-(prop-2'-inyl)-β-D-arabino-hexopyranose (190188-95-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 89 percent / pyridine / CH₂Cl₂ / 3 h / Heating

2.1: NaH / tetrahydrofuran; various solvent(s) / 0 °C

2.2: 820 mg / tetrahydrofuran; various solvent(s) / cooling

With pyridine; sodium hydride; In tetrahydrofuran; dichloromethane; 1.1: Condensation / 2.1: Metallation / 2.2: Alkylation;

DOI:10.1021/jo000325y

upstream raw materials:

propargyl bromide

(3Z)-1,6-anhydro-4-O-(tert-butyldiphenylsilyl)-3-deoxy-3-methoxyimine-β-D-arabino-hexopyranose

D-Mannose

(1R,2S,3R,4S,5R)-2-(tert-Butyl-diphenyl-silanyloxy)-6,8-dioxa-bicyclo[3.2.1]octane-3,4-diol