3-[(4R,5R)-5-benzyloxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl]propionic acid methyl ester

Base Information

• Chemical Name: 3-[(4R,5R)-5-benzyloxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl]propionic acid methyl ester
• CAS No.: 850222-13-8
• Molecular Formula: C₁₇H₂₄O₅
• Molecular Weight: 308.375
• Mol file: 850222-13-8.mol

Synonyms:3-[(4R,5R)-5-benzyloxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl]propionic acid methyl ester

Chemical Property of 3-[(4R,5R)-5-benzyloxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl]propionic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-[(4R,5R)-5-benzyloxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl]propionic acid methyl ester

There total 8 articles about 3-[(4R,5R)-5-benzyloxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl]propionic acid methyl ester 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: 93.0%

methanol (67-56-1) + 2,2-dimethoxy-propane (77-76-9) + (5R)-5-[(1R)-2-benzyloxy-1-hydroxyethyl]tetrahydrofuran-2-one (754188-59-5) → 3-[(4R,5R)-5-benzyloxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl]propionic acid methyl ester (850222-13-8)

Guidance literature:

With toluene-4-sulfonic acid; at 20 ℃; for 3h;

DOI:10.1016/j.tetlet.2005.01.052

Reference yield:

benzyl bromide (100-39-0) → 3-[(4R,5R)-5-benzyloxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl]propionic acid methyl ester (850222-13-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: NaH; TBAI / tetrahydrofuran

1.2: 48 percent / EtCOOH / 2 h / Heating

2.1: 95 percent / aq. LiOH / tetrahydrofuran

3.1: AD-mix-β; MeSO2NH2 / 2-methyl-propan-2-ol; H2O

3.2: HCl / acetone

With lithium hydroxide; methanesulfonamide; AD-mix-β; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; water; tert-butyl alcohol; 1.2: Claisen rearrangement / 3.1: Sharpless asymmetric dihydroxylation;

DOI:10.1016/j.tet.2005.05.057

Reference yield:

(E)-6-benzyloxyhex-4-enoic acid methyl ester (692753-37-0) → 3-[(4R,5R)-5-benzyloxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl]propionic acid methyl ester (850222-13-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 95 percent / aq. LiOH / tetrahydrofuran

2.1: AD-mix-β; MeSO2NH2 / 2-methyl-propan-2-ol; H2O

2.2: HCl / acetone

With lithium hydroxide; methanesulfonamide; AD-mix-β; In tetrahydrofuran; water; tert-butyl alcohol; 2.1: Sharpless asymmetric dihydroxylation;

DOI:10.1016/j.tet.2005.05.057

upstream raw materials:

methanol

2,2-dimethoxy-propane

(5R)-5-[(1R)-2-benzyloxy-1-hydroxyethyl]tetrahydrofuran-2-one

(E)-6-Benzyloxy-hex-4-enoic acid

Downstream raw materials:

(5R)-5-[(1R)-2-benzyloxy-1-hydroxyethyl]tetrahydrofuran-2-one