ethyl (2S,3S)-2-O-benzyl-3,4-O-isopropylidene-2,3,4-trihydroxybutanoate

Base Information

• Chemical Name: ethyl (2S,3S)-2-O-benzyl-3,4-O-isopropylidene-2,3,4-trihydroxybutanoate
• CAS No.: 340699-15-2
• Molecular Formula: C₁₆H₂₂O₅
• Molecular Weight: 294.348
• Mol file: 340699-15-2.mol

Synonyms:ethyl (2S,3S)-2-O-benzyl-3,4-O-isopropylidene-2,3,4-trihydroxybutanoate

Chemical Property of ethyl (2S,3S)-2-O-benzyl-3,4-O-isopropylidene-2,3,4-trihydroxybutanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of ethyl (2S,3S)-2-O-benzyl-3,4-O-isopropylidene-2,3,4-trihydroxybutanoate

There total 4 articles about ethyl (2S,3S)-2-O-benzyl-3,4-O-isopropylidene-2,3,4-trihydroxybutanoate 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: 88.0%

benzyl bromide (100-39-0) + ethyl (2S,3S)-3,4-O-isopropylidene-2,3,4-trihydroxybutanoate (340699-14-1) → ethyl (2S,3S)-2-O-benzyl-3,4-O-isopropylidene-2,3,4-trihydroxybutanoate (340699-15-2)

Guidance literature:

With silver(l) oxide; potassium iodide; In toluene; for 1.5h; Heating;

DOI:10.1002/1099-0690(200104)2001:7<1335::AID-EJOC1335>3.0.CO;2-Z

Reference yield:

ethyl (2R)-2-[(1S)-3,3-dimethyl(2,4-dioxolanyl)]-2-hydroxyacetate (114185-07-8) → ethyl (2S,3S)-2-O-benzyl-3,4-O-isopropylidene-2,3,4-trihydroxybutanoate (340699-15-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 73 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 12 h / 20 °C

2: 90 percent / triethylamine; ethanol

3: 80 percent / silver(I) oxide; tetrabutylammonium iodide / acetonitrile / 12 h / Heating

With ethanol; di-isopropyl azodicarboxylate; tetra-(n-butyl)ammonium iodide; triethylamine; triphenylphosphine; silver(l) oxide; In tetrahydrofuran; acetonitrile; 1: Mitsunobu reaction;

DOI:10.1021/jo0521192

Reference yield:

(R)-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-trifluoromethanesulfonyloxy-acetic acid ethyl ester (205489-00-5) → ethyl (2S,3S)-2-O-benzyl-3,4-O-isopropylidene-2,3,4-trihydroxybutanoate (340699-15-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 4.93 g / Bu₄NNO₂ / CH₂Cl₂ / 1 h / 40 °C

2: 88 percent / Ag₂O / KI / toluene / 1.5 h / Heating

With tetrabutylammonium nitrite; silver(l) oxide; potassium iodide; In dichloromethane; toluene;

DOI:10.1002/1099-0690(200104)2001:7<1335::AID-EJOC1335>3.0.CO;2-Z

upstream raw materials:

benzyl bromide

ethyl (2S,3S)-3,4-O-isopropylidene-2,3,4-trihydroxybutanoate

(S)-(2-Chloro-acetoxy)-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-acetic acid ethyl ester

ethyl (2R)-2-[(1S)-3,3-dimethyl(2,4-dioxolanyl)]-2-hydroxyacetate

Downstream raw materials:

(R)-2-Benzyloxy-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethanol

(6S,7S,8S)-7,8-Bis-benzyloxy-5,6,7,8-tetrahydro-imidazo[1,5-a]pyridin-6-ol

(6S,7S,8R)-7,8-Bis-benzyloxy-5,6,7,8-tetrahydro-imidazo[1,5-a]pyridin-6-ol

(2S,3S,4R)-3,4-Bis-benzyloxy-4-(3H-imidazol-4-yl)-butane-1,2-diol