tert-butyl 2-((4R,6S)-6-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxane-4-yl)acetate

Base Information

• Chemical Name: tert-butyl 2-((4R,6S)-6-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxane-4-yl)acetate
• CAS No.: 151140-38-4
• Molecular Formula: C₂₀H₃₀O₅
• Molecular Weight: 350.455
• Mol file: 151140-38-4.mol

Synonyms:tert-butyl 2-((4R,6S)-6-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxane-4-yl)acetate

Chemical Property of tert-butyl 2-((4R,6S)-6-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxane-4-yl)acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl 2-((4R,6S)-6-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxane-4-yl)acetate

There total 7 articles about tert-butyl 2-((4R,6S)-6-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxane-4-yl)acetate 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: 96.0%

2,2-dimethoxy-propane (77-76-9) + (3R,5S)-6-benzyloxy-3,5-dihydroxy-hexanoic acid tert-butyl ester (153716-95-1) → tert-butyl 2-((4R,6S)-6-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxane-4-yl)acetate (151140-38-4)

Guidance literature:

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

DOI:10.1021/jo201822k

Reference yield: 77.0%

2,2-dimethoxy-propane (77-76-9) + 6-benzyloxy-3,5-dihydroxy-hexanoic acid tert-butyl ester → tert-butyl 2-((4R,6S)-6-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxane-4-yl)acetate (151140-38-4)

Guidance literature:

2,2-dimethoxy-propane; 6-benzyloxy-3,5-dihydroxy-hexanoic acid tert-butyl ester; With camphor-10-sulfonic acid; In acetone; at 20 ℃; for 2h;

With hydrogenchloride; In dichloromethane; at 20 ℃; for 3h; Further stages.;

DOI:10.1021/ol017223u

Reference yield:

tert-butyl (S)-6-(benzyloxy)-5-hydroxy-3-oxohexanoate (147849-64-7) → tert-butyl 2-((4R,6S)-6-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxane-4-yl)acetate (151140-38-4)

Guidance literature:

Multi-step reaction with 2 steps

1: methanol; diethyl methoxy borane; sodium tetrahydroborate / tetrahydrofuran / 2.5 h / -80 - -70 °C / Inert atmosphere

2: methanesulfonic acid / 20 °C

With methanol; sodium tetrahydroborate; methanesulfonic acid; diethyl methoxy borane; In tetrahydrofuran;

upstream raw materials:

2,2-dimethoxy-propane

(3R,5S)-6-benzyloxy-3,5-dihydroxy-hexanoic acid tert-butyl ester

acetic acid tert-butyl ester

tert-butyl (S)-4-(propylene oxide-2-yl)-3-oxobutanoate

Downstream raw materials:

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate