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

Base Information

• Chemical Name: ethyl (2R,3S)-2-O-benzyl-3,4-O-isopropylidene-2,3,4-trihydroxybutanoate
• CAS No.: 340699-28-7
• Molecular Formula: C₁₆H₂₂O₅
• Molecular Weight: 294.348
• Mol file: 340699-28-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 6 articles about ethyl (2R,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: 91.0%

benzyl bromide (100-39-0) + ethyl (2R)-2-[(1S)-3,3-dimethyl(2,4-dioxolanyl)]-2-hydroxyacetate (114185-07-8) → ethyl (2R,3S)-2-O-benzyl-3,4-O-isopropylidene-2,3,4-trihydroxybutanoate (340699-28-7)

Guidance literature:

ethyl (2R)-2-[(1S)-3,3-dimethyl(2,4-dioxolanyl)]-2-hydroxyacetate; With 4 A molecular sieve; potassium iodide; silver(l) oxide; In toluene; at 50 ℃;

benzyl bromide; for 2h; Further stages.; Heating;

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

Reference yield:

5,6-O-isopropylidene-L-ascorbic acid (15042-01-0) → ethyl (2R,3S)-2-O-benzyl-3,4-O-isopropylidene-2,3,4-trihydroxybutanoate (340699-28-7)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium carbonate; dihydrogen peroxide / water

2: acetonitrile

3: silver(l) oxide / dichloromethane

With dihydrogen peroxide; potassium carbonate; silver(l) oxide; In dichloromethane; water; acetonitrile;

Reference yield:

O3,O4-(1-methylethylidene)-L-threonic acid (92973-39-2,136136-17-9) → ethyl (2R,3S)-2-O-benzyl-3,4-O-isopropylidene-2,3,4-trihydroxybutanoate (340699-28-7)

Guidance literature:

Multi-step reaction with 2 steps

1: acetonitrile

2: silver(l) oxide / dichloromethane

With silver(l) oxide; In dichloromethane; acetonitrile;

upstream raw materials:

benzyl bromide

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

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

5,6-O-isopropylidene-L-ascorbic acid

Downstream raw materials:

2-O-benzyl-3,4-O-isopropylidene-L-threitol

(4S,Z)-ethyl 4-(benzyloxy)-4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)but-2-enoate

(4S,E)-ethyl 4-(benzyloxy)-4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)but-2-enoate

(2R,3S,4R,5S)-2,3:5,6-di(O-isopropylidene)-4-O-benzyl-2,3,4,5,6-pentahydroxyhexanal