ethyl (2E)-3-{(4R,5R)-5-[(benzyloxy)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}acrylate

Base Information

• Chemical Name: ethyl (2E)-3-{(4R,5R)-5-[(benzyloxy)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}acrylate
• CAS No.: 91548-58-2
• Molecular Formula: C₁₈H₂₄O₅
• Molecular Weight: 320.386

Synonyms:ethyl (2E)-3-{(4R,5R)-5-[(benzyloxy)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}acrylate

Chemical Property of ethyl (2E)-3-{(4R,5R)-5-[(benzyloxy)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}acrylate

Chemical Property:

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Technology Process of ethyl (2E)-3-{(4R,5R)-5-[(benzyloxy)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}acrylate

There total 16 articles about ethyl (2E)-3-{(4R,5R)-5-[(benzyloxy)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}acrylate 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: 90.0%

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) + 4-O-benzyl-2,3-O-isopropylidene-D-threose (81801-09-4) → ethyl (2E)-3-{(4R,5R)-5-[(benzyloxy)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}acrylate (91548-58-2)

Guidance literature:

diethoxyphosphoryl-acetic acid ethyl ester; With sodium hydride; In tetrahydrofuran; at 0 ℃; for 0.5h; Inert atmosphere;

4-O-benzyl-2,3-O-isopropylidene-D-threose; In tetrahydrofuran; at 0 ℃; for 2h; Inert atmosphere;

DOI:10.1055/s-0035-1561431

Reference yield: 90.0%

(4R,5S)-4-(benzyloxymethyl)-5-(chloromethyl)-2,2-dimethyl-1,3-di-oxolane (1374433-25-6) + ethyl (triphenylphosphoranylidene)acetate (1099-45-2) → ethyl (2E)-3-{(4R,5R)-5-[(benzyloxy)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}acrylate (91548-58-2)

Guidance literature:

In benzene; at 20 ℃; for 6h;

DOI:10.1016/j.tetlet.2014.02.096

Reference yield: 88.0%

(4S,5R)-4-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane-5-carboxaldehyde (81028-12-8) + ethyl (triphenylphosphoranylidene)acetate (1099-45-2) → ethyl 3-((4S,5S)-5-(benzyloxy methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate (90661-38-4,90661-39-5,91548-58-2,91548-59-3)

Guidance literature:

In methanol; Ambient temperature;

DOI:10.1016/S0040-4020(01)97597-0

upstream raw materials:

(4S,5R)-4-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane-5-carboxaldehyde

ethyl (triphenylphosphoranylidene)acetate

(4S,5S)-4-benzyloxymethyl-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolane

2,3-O-isopropylidene-L-threitol

Downstream raw materials:

(S)-5-((S)-2'-(benzyloxy)-1-hydroxyethyl)furan-2(5H)-one

(5S,6S)-6-Benzyloxymethyl-5-hydroxy-5,6-dihydro-pyran-2-one

(E)-3-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-prop-2-en-1-ol

(-)-Se-phenyl (4S,5S)-4,5-(isopropylidenedioxy)selenohept-6-enoate

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