(1R,2S,3R,4R)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-(4,5-dimethyl-furan-2-yl)-2,4-dimethyl-pentan-1-ol

Base Information

• Chemical Name: (1R,2S,3R,4R)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-(4,5-dimethyl-furan-2-yl)-2,4-dimethyl-pentan-1-ol
• CAS No.: 85880-74-6
• Molecular Formula: C₂₆H₄₂O₄Si
• Molecular Weight: 446.703
• Mol file: 85880-74-6.mol

Synonyms:(1R,2S,3R,4R)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-(4,5-dimethyl-furan-2-yl)-2,4-dimethyl-pentan-1-ol

Chemical Property of (1R,2S,3R,4R)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-(4,5-dimethyl-furan-2-yl)-2,4-dimethyl-pentan-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2S,3R,4R)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-(4,5-dimethyl-furan-2-yl)-2,4-dimethyl-pentan-1-ol

There total 9 articles about (1R,2S,3R,4R)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-(4,5-dimethyl-furan-2-yl)-2,4-dimethyl-pentan-1-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:

5-[(1S,2R,3R,4R)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-1-trimethylsilanyloxy-pentyl]-2,3-dimethyl-furan → (1S,2S,3R,4R)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-(4,5-dimethyl-furan-2-yl)-2,4-dimethyl-pentan-1-ol (85828-13-3,85880-74-6,134931-87-6)

Guidance literature:

With potassium carbonate; In methanol; at 20 ℃; for 1.25h; Yield given;

DOI:10.1016/S0040-4039(00)74320-6

Reference yield:

4,5-dimethyl-2-formylfuran (52480-43-0) → (1S,2S,3R,4R)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-(4,5-dimethyl-furan-2-yl)-2,4-dimethyl-pentan-1-ol (85828-13-3,85880-74-6,134931-87-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 2) aq. H₂O₂, pH₇ buffer / 1) CH₂Cl₂, 0 deg C, 12 h; 2) MeOH, 1 h

2: 100 percent / Me₄N*HB(OAc)3 / acetonitrile; acetic acid / 12 h / -20 °C

3: 77 percent / tetrahydrofuran / -78 deg C, then 20 deg C, 40 min

4: 2,6-lutidine / CH₂Cl₂ / 0.75 h / -78 °C

5: K₂CO₃ / methanol / 1.25 h / 20 °C

With 2,6-dimethylpyridine; pH₇ buffer; dihydrogen peroxide; potassium carbonate; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; methanol; dichloromethane; acetic acid; acetonitrile;

DOI:10.1016/S0040-4039(00)74320-6

Reference yield:

(1S,2R,3R,4R)-5-Benzyloxy-1-(4,5-dimethyl-furan-2-yl)-2,4-dimethyl-pentane-1,3-diol (134860-58-5) → (1S,2S,3R,4R)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-(4,5-dimethyl-furan-2-yl)-2,4-dimethyl-pentan-1-ol (85828-13-3,85880-74-6,134931-87-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 77 percent / tetrahydrofuran / -78 deg C, then 20 deg C, 40 min

2: 2,6-lutidine / CH₂Cl₂ / 0.75 h / -78 °C

3: K₂CO₃ / methanol / 1.25 h / 20 °C

With 2,6-dimethylpyridine; potassium carbonate; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/S0040-4039(00)74320-6

upstream raw materials:

2,3-dimethylfuran

(2S,3S,4S)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-pentanal

(2R,3S,4S)-1-Benzyloxy-2,4-dimethyl-hex-5-en-3-ol

tert-butyldimethylsilyl chloride

Downstream raw materials:

(S)-2-[(1S,2R,3R)-4-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-1,3-dimethyl-butyl]-6-hydroxy-5,6-dimethyl-6H-pyran-3-one

(1S,3R,4R,5S)-3-((R)-2-Benzyloxy-1-methyl-ethyl)-1,4,8-trimethyl-2,9-dioxa-bicyclo[3.3.1]non-7-en-6-one

(1S,2S,3R,4R)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-(4,5-dimethyl-furan-2-yl)-2,4-dimethyl-pentan-1-ol

(1R,3S,4S,5R)-3-((S)-2-Benzyloxy-1-methyl-ethyl)-1,4,8-trimethyl-2,9-dioxa-bicyclo[3.3.1]non-7-en-6-one