(2R,3S)-3-O-benzyl-1-O-tert-butyldiphenylsilyl-4-pentene-1,2,3-triol

Base Information

• Chemical Name: (2R,3S)-3-O-benzyl-1-O-tert-butyldiphenylsilyl-4-pentene-1,2,3-triol
• CAS No.: 220788-29-4
• Molecular Formula: C₂₈H₃₄O₃Si
• Molecular Weight: 446.662
• Mol file: 220788-29-4.mol

Synonyms:(2R,3S)-3-O-benzyl-1-O-tert-butyldiphenylsilyl-4-pentene-1,2,3-triol

Chemical Property of (2R,3S)-3-O-benzyl-1-O-tert-butyldiphenylsilyl-4-pentene-1,2,3-triol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-3-O-benzyl-1-O-tert-butyldiphenylsilyl-4-pentene-1,2,3-triol

There total 5 articles about (2R,3S)-3-O-benzyl-1-O-tert-butyldiphenylsilyl-4-pentene-1,2,3-triol 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: 95.0%

(2R,3S)-3-O-benzyl-4-pentene-1,2,3-triol (115586-67-9) + tert-butylchlorodiphenylsilane (58479-61-1) → (2R,3S)-3-O-benzyl-1-O-tert-butyldiphenylsilyl-4-pentene-1,2,3-triol (220788-29-4)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(98)02561-1

Reference yield:

(4R)-1-(2,2-dimethyl-[1,3]dioxolan-4-yl)allyl alcohol (212579-64-1) → (2R,3S)-3-O-benzyl-1-O-tert-butyldiphenylsilyl-4-pentene-1,2,3-triol (220788-29-4)

Guidance literature:

Multi-step reaction with 3 steps

1: NaH / tetrahydrofuran

2: 100 percent / Dowex 50 W/H⁺ acid resin / methanol / 2 h / 20 °C

3: 95 percent / imidazole / dimethylformamide / 0.83 h

With 1H-imidazole; Dowex 50 W; H⁺ acid resin; sodium hydride; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1002/1099-0690(200102)2001:3<507::AID-EJOC507>3.0.CO;2-R

Reference yield:

(+)-(3S,4R)-3-benzyloxy-4,5-O-isopropylidene-4,5-dihydroxy-1-pentene (108275-52-1) → (2R,3S)-3-O-benzyl-1-O-tert-butyldiphenylsilyl-4-pentene-1,2,3-triol (220788-29-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / Dowex 50 W/H⁺ acid resin / methanol / 2 h / 20 °C

2: 95 percent / imidazole / dimethylformamide / 0.83 h

With 1H-imidazole; Dowex 50 W; H⁺ acid resin; In methanol; N,N-dimethyl-formamide;

DOI:10.1002/1099-0690(200102)2001:3<507::AID-EJOC507>3.0.CO;2-R

upstream raw materials:

(2R,3S)-3-O-benzyl-4-pentene-1,2,3-triol

tert-butylchlorodiphenylsilane

benzyl bromide

(4R)-1-(2,2-dimethyl-[1,3]dioxolan-4-yl)allyl alcohol

Downstream raw materials:

(2R,3R)-3-benzyloxy-2-(tert-butyldiphenylsilyloxymethyl)-4-(phenylselenyl)tetrahydrofuran