[(2S,3R,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-2-(1,2-dihydroxy-ethyl)-tetrahydro-furan-3-yl]-acetic acid ethyl ester

Base Information

• Chemical Name: [(2S,3R,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-2-(1,2-dihydroxy-ethyl)-tetrahydro-furan-3-yl]-acetic acid ethyl ester
• CAS No.: 101069-37-8
• Molecular Formula: C₂₆H₃₆O₆Si
• Molecular Weight: 472.654
• Mol file: 101069-37-8.mol

Synonyms:[(2S,3R,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-2-(1,2-dihydroxy-ethyl)-tetrahydro-furan-3-yl]-acetic acid ethyl ester

Chemical Property of [(2S,3R,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-2-(1,2-dihydroxy-ethyl)-tetrahydro-furan-3-yl]-acetic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(2S,3R,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-2-(1,2-dihydroxy-ethyl)-tetrahydro-furan-3-yl]-acetic acid ethyl ester

There total 7 articles about [(2S,3R,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-2-(1,2-dihydroxy-ethyl)-tetrahydro-furan-3-yl]-acetic acid ethyl ester 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: 92.0%

1,4-anhydro-2-O-tert-butyldiphenylsilyl-3-deoxy-3-C-(ethoxycarbonylmethyl)-5,6-O-isopropylidene-D-allitol (101069-28-7,101144-07-4) → [(2S,3R,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-2-(1,2-dihydroxy-ethyl)-tetrahydro-furan-3-yl]-acetic acid ethyl ester (101069-37-8)

Guidance literature:

With acetic acid; In water; for 10h; Ambient temperature;

DOI:10.1016/S0008-6215(00)90454-3

Reference yield:

1,4-anhydro-2-O-tert-butyldiphenylsilyl-5,6-O-isopropylidene-D-glucitol (101069-26-5) → [(2S,3R,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-2-(1,2-dihydroxy-ethyl)-tetrahydro-furan-3-yl]-acetic acid ethyl ester (101069-37-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 98 percent / 1-ethyl-3-(3'-dimethylaminopropyl)carbodi-imide hydrochloride, dichloroacetic acid / dimethylsulfoxide / 3 h / Ambient temperature

2: CH₂Cl₂ / 12 h / Ambient temperature

3: H₂ / 10percent Pd/C / ethanol / 16 h

4: 92 percent / 70percent acetic acid / H₂O / 10 h / Ambient temperature

With dichloro-acetic acid; hydrogen; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal; In ethanol; dichloromethane; water; dimethyl sulfoxide;

DOI:10.1016/S0008-6215(00)90454-3

Reference yield:

1,4-anhydro-2-O-tert-butyldiphenylsilyl-5,6-O-isopropylidene-D-ribo-3-hexulose (101125-99-9) → [(2S,3R,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-2-(1,2-dihydroxy-ethyl)-tetrahydro-furan-3-yl]-acetic acid ethyl ester (101069-37-8)

Guidance literature:

Multi-step reaction with 3 steps

1: CH₂Cl₂ / 12 h / Ambient temperature

2: H₂ / 10percent Pd/C / ethanol / 16 h

3: 92 percent / 70percent acetic acid / H₂O / 10 h / Ambient temperature

With hydrogen; acetic acid; palladium on activated charcoal; In ethanol; dichloromethane; water;

DOI:10.1016/S0008-6215(00)90454-3

upstream raw materials:

1,4-anhydro-2-O-tert-butyldiphenylsilyl-3-deoxy-3-C-(ethoxycarbonylmethyl)-5,6-O-isopropylidene-D-allitol

1,4-anhydro-2-O-tert-butyldiphenylsilyl-5,6-O-isopropylidene-D-glucitol

1,4-anhydro-2-O-tert-butyldiphenylsilyl-5,6-O-isopropylidene-D-ribo-3-hexulose

1,4-anhydro-2-O-tert-butyldiphenylsilyl-3-deoxy-3-C-(ethoxycarbonylmethylene)-5,6-O-isopropylidene-D-ribo-hexitol

Downstream raw materials:

1,4-anhydro-2-O-tert-butyldiphenylsilyl-3,5-dideoxy-3-C-(ethoxycarbonylmethyl)-5-C-(2-oxo-trans-heptylidene)-D-ribitol

[(2S,3R,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-2-formyl-tetrahydro-furan-3-yl]-acetic acid ethyl ester