tert-butyl 2-[(6S,4R)-6-(hydroxymethyl)-2-(4-methoxyphenyl)-1,3-dioxan-4-yl]acetate

Base Information

• Chemical Name: tert-butyl 2-[(6S,4R)-6-(hydroxymethyl)-2-(4-methoxyphenyl)-1,3-dioxan-4-yl]acetate
• CAS No.: 625124-76-7
• Molecular Formula: C₁₈H₂₆O₆
• Molecular Weight: 338.401
• Mol file: 625124-76-7.mol

Synonyms:tert-butyl 2-[(6S,4R)-6-(hydroxymethyl)-2-(4-methoxyphenyl)-1,3-dioxan-4-yl]acetate

Chemical Property of tert-butyl 2-[(6S,4R)-6-(hydroxymethyl)-2-(4-methoxyphenyl)-1,3-dioxan-4-yl]acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl 2-[(6S,4R)-6-(hydroxymethyl)-2-(4-methoxyphenyl)-1,3-dioxan-4-yl]acetate

There total 7 articles about tert-butyl 2-[(6S,4R)-6-(hydroxymethyl)-2-(4-methoxyphenyl)-1,3-dioxan-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: 89.0%

tert-butyl 2-{(6S,4R)-2-(4-methoxyphenyl)-6-[(phenylmethoxy)methyl]-1,3-dioxan-4-yl}acetate (862465-63-2) → tert-butyl 2-[(6S,4R)-6-(hydroxymethyl)-2-(4-methoxyphenyl)-1,3-dioxan-4-yl]acetate (625124-76-7)

Guidance literature:

With hydrogen; nickel; In ethanol; at 20 ℃; for 3h; under 760 Torr;

DOI:10.1021/ol051225n

Reference yield:

tert-butyl 2-((6S,4R)-6-{[1,1-bis(1-methylethyl)-2-methyl-1-silapropoxy]methyl}-2-(4-methoxyphenyl)-1,3-dioxan-4-yl)acetate (862465-84-7) → tert-butyl 2-[(6S,4R)-6-(hydroxymethyl)-2-(4-methoxyphenyl)-1,3-dioxan-4-yl]acetate (625124-76-7)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 1h;

DOI:10.1021/ja030316h

Reference yield:

acetic acid tert-butyl ester (540-88-5) → tert-butyl 2-[(6S,4R)-6-(hydroxymethyl)-2-(4-methoxyphenyl)-1,3-dioxan-4-yl]acetate (625124-76-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: LDA / tetrahydrofuran; hexane / 1 h

1.2: tetrahydrofuran; hexane / 0.5 h / Heating

2.1: 87.3 g / Et₂BOMe; NaBH₄ / tetrahydrofuran; methanol

3.1: PPTS / CH₂Cl₂ / 2.5 h / Heating

4.1: 33.0 g / tetrabutylammonium fluoride trihydrate / tetrahydrofuran / 1 h

With sodium tetrahydroborate; diethyl methoxy borane; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; dichloromethane; 1.2: Claisen condensation;

DOI:10.1021/ja030316h

upstream raw materials:

tert-butyl 2-((6S,4R)-6-{[1,1-bis(1-methylethyl)-2-methyl-1-silapropoxy]methyl}-2-(4-methoxyphenyl)-1,3-dioxan-4-yl)acetate

tert-butyl 2-{(6S,4R)-2-(4-methoxyphenyl)-6-[(phenylmethoxy)methyl]-1,3-dioxan-4-yl}acetate

p-Anisaldehyde dimethyl acetal

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

Downstream raw materials:

[(2R,4S,6R,8R,10S)-4-acetoxy-8-{2-[2-((1S)-4-methoxybenzyloxy)-1-methylethyl]-allyl}-10-methyl-10-triethylsilanyloxy-1,7-dioxaspiro[5.5]undec-2-yl]acetic acid tert-butyl ester

[(2R,4R,6S)-6-((Z)-(R)-7-Benzyloxy-4-hydroxy-2-oxo-6-triethylsilanyloxy-hept-3-enyl)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-acetic acid tert-butyl ester

[(2R,4R,6S)-6-((2RS,6R)-7-benzyloxy-2-hydroxy-4-oxo-6-triethylsilanyloxyheptyl)-2-(4-methoxyphenyl)-[1,3]dioxan-4-yl]acetic acid tert-butyl ester

[(2R,4S,6R,8R,10S)-8-benzyloxymethyl-4,10-dihydroxy-10-methyl-1,7-dioxaspiro[5.5]undec-2-yl]acetic acid tert-butyl ester