(2S,3R)-tert-butyl 2-(benzyloxy)-3-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)pent-4-enoate

Base Information

• Chemical Name: (2S,3R)-tert-butyl 2-(benzyloxy)-3-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)pent-4-enoate
• CAS No.: 1265592-08-2
• Molecular Formula: C₂₁H₃₀O₅
• Molecular Weight: 362.466
• Mol file: 1265592-08-2.mol

Synonyms:(2S,3R)-tert-butyl 2-(benzyloxy)-3-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)pent-4-enoate

Chemical Property of (2S,3R)-tert-butyl 2-(benzyloxy)-3-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)pent-4-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-tert-butyl 2-(benzyloxy)-3-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)pent-4-enoate

There total 6 articles about (2S,3R)-tert-butyl 2-(benzyloxy)-3-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)pent-4-enoate 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: 99.0%

tert-butyl (2S,3S)-3-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-hydroxypent-4-enoate (1266545-65-6) + benzyl bromide (100-39-0) → (2S,3R)-tert-butyl 2-(benzyloxy)-3-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)pent-4-enoate (1265592-08-2)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride;

DOI:10.1021/ml100289m

Reference yield:

tert-butyl (R,Z)-2-((3-(2,2-dimethyl-1,3-dioxolan-4-yl)allyl)oxy)acetate (1265592-06-0) → (2S,3R)-tert-butyl 2-(benzyloxy)-3-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)pent-4-enoate (1265592-08-2)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium tert-butylate / -10 °C

2: tetra-(n-butyl)ammonium iodide; sodium hydride

With potassium tert-butylate; tetra-(n-butyl)ammonium iodide; sodium hydride;

DOI:10.1021/ml100289m

Reference yield:

(R,Z)-3-(2′,2′-dimethyl-1′,3′-dioxolan-4′-yl)prop-2-en-1-ol (106757-58-8) → (2S,3R)-tert-butyl 2-(benzyloxy)-3-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)pent-4-enoate (1265592-08-2)

Guidance literature:

Multi-step reaction with 3 steps

1: cesium hydroxide; tetra-(n-butyl)ammonium iodide / water; acetonitrile / Molecular sieve

2: potassium tert-butylate / -10 °C

3: tetra-(n-butyl)ammonium iodide; sodium hydride

With cesium hydroxide; potassium tert-butylate; tetra-(n-butyl)ammonium iodide; sodium hydride; In water; acetonitrile;

DOI:10.1021/ml100289m

upstream raw materials:

tert-butyl (R,Z)-2-((3-(2,2-dimethyl-1,3-dioxolan-4-yl)allyl)oxy)acetate

tert-butyl (2S,3S)-3-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-hydroxypent-4-enoate

benzyl bromide

(R,Z)-3-(2′,2′-dimethyl-1′,3′-dioxolan-4′-yl)prop-2-en-1-ol

Downstream raw materials:

(3R,3aR,4S,6aS)-4-(benzyloxy)hexahydrofuro[2,3-b]furan-3-ol

(3R,3aS,4S,6aR)-4-(benzyloxy)hexahydrofuro[2,3-b]furan-3-yl-(2S,3R)-3-hydroxy-4-(N-isobutyl-4-methoxyphenylsulfonamido)-1-phenylbutan-2-ylcarbamate