(1S,2S)-1-(tert-butyldiphenylsilanyloxy)methyl-2-hydroxymethylcyclopropane

Base Information

• Chemical Name: (1S,2S)-1-(tert-butyldiphenylsilanyloxy)methyl-2-hydroxymethylcyclopropane
• CAS No.: 408348-57-2
• Molecular Formula: C₂₁H₂₈O₂Si
• Molecular Weight: 340.538
• Mol file: 408348-57-2.mol

Synonyms:(1S,2S)-1-(tert-butyldiphenylsilanyloxy)methyl-2-hydroxymethylcyclopropane

Chemical Property of (1S,2S)-1-(tert-butyldiphenylsilanyloxy)methyl-2-hydroxymethylcyclopropane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S)-1-(tert-butyldiphenylsilanyloxy)methyl-2-hydroxymethylcyclopropane

There total 5 articles about (1S,2S)-1-(tert-butyldiphenylsilanyloxy)methyl-2-hydroxymethylcyclopropane 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:

diiodomethane (75-11-6) + (E)-4-(tert-butyldiphenylsilyloxy)-2-buten-1-ol (92808-78-1) → (1R,2R)-2-<<(tert-Butyldiphenylsilyl)oxy>methyl>-1-(hydroxymethyl)cyclopropane (154001-59-9) + (1S,2S)-1-(tert-butyldiphenylsilanyloxy)methyl-2-hydroxymethylcyclopropane (408348-57-2)

Guidance literature:

With diethylzinc; diethylaluminium chloride; In hexane; dichloromethane; at 20 ℃; for 3h; Title compound not separated from byproducts.;

DOI:10.1002/anie.200705641

Reference yield:

(1S,2R)-2-(tert-butyldiphenylsilyloxy)methyl-1-hydroxymethyl-1-phenylsulfonylcyclopropane (408348-56-1) → (1S,2S)-1-(tert-butyldiphenylsilanyloxy)methyl-2-hydroxymethylcyclopropane (408348-57-2)

Guidance literature:

With magnesium; In methanol; at 50 ℃;

DOI:10.1021/jo010852x

Reference yield:

(1S,5R)-2-oxo-1-phenylsulfonyl-3-oxabicyclo[3.1.0]hexane (409307-02-4) → (1S,2S)-1-(tert-butyldiphenylsilanyloxy)methyl-2-hydroxymethylcyclopropane (408348-57-2)

Guidance literature:

Multi-step reaction with 3 steps

1: NaBH₄ / methanol; tetrahydrofuran / 20 °C

2: imidazole / dimethylformamide / -20 °C

3: Mg / methanol / 50 °C

With 1H-imidazole; sodium tetrahydroborate; magnesium; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1021/jo010852x

upstream raw materials:

(1S,2R)-2-(tert-butyldiphenylsilyloxy)methyl-1-hydroxymethyl-1-phenylsulfonylcyclopropane

(1S,5R)-2-oxo-1-phenylsulfonyl-3-oxabicyclo[3.1.0]hexane

(1S,2R)-1,2-bis(hydroxymethyl)-1-phenylsulfonylcyclopropane

diiodomethane

Downstream raw materials:

(+)-(1S,2S) methyl 2-formylcyclopropanecarboxylate

(1S,2S)-2-(tert-butyldiphenylsilyloxy)methyl-1-formylcyclopropane