4-[(4S,6R)-6-(2-Benzyloxy-1,1-dimethyl-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-3-hydroxy-2-methyl-butyric acid methyl ester

Base Information

• Chemical Name: 4-[(4S,6R)-6-(2-Benzyloxy-1,1-dimethyl-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-3-hydroxy-2-methyl-butyric acid methyl ester
• CAS No.: 909016-30-4
• Molecular Formula: C₂₃H₃₆O₆
• Molecular Weight: 408.535
• Mol file: 909016-30-4.mol

Synonyms:4-[(4S,6R)-6-(2-Benzyloxy-1,1-dimethyl-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-3-hydroxy-2-methyl-butyric acid methyl ester

Chemical Property of 4-[(4S,6R)-6-(2-Benzyloxy-1,1-dimethyl-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-3-hydroxy-2-methyl-butyric acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-[(4S,6R)-6-(2-Benzyloxy-1,1-dimethyl-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-3-hydroxy-2-methyl-butyric acid methyl ester

There total 8 articles about 4-[(4S,6R)-6-(2-Benzyloxy-1,1-dimethyl-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-3-hydroxy-2-methyl-butyric 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: 88.0%

Methyl 2-bromopropionate (5445-17-0) + [(4R,6R)-6-(2-Benzyloxy-1,1-dimethyl-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-acetaldehyde (121352-96-3) → 4-[(4S,6R)-6-(2-Benzyloxy-1,1-dimethyl-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-3-hydroxy-2-methyl-butyric acid methyl ester (909016-30-4)

Guidance literature:

With RhCl(PPh₃)3; diethylzinc; In tetrahydrofuran; hexane; at 0 ℃; for 0.583333h;

DOI:10.1016/j.tet.2006.05.077

Reference yield:

propanoic acid methyl ester (554-12-1) + [(4R,6R)-6-(2-Benzyloxy-1,1-dimethyl-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-acetaldehyde (121352-96-3) → 4-[(4S,6R)-6-(2-Benzyloxy-1,1-dimethyl-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-3-hydroxy-2-methyl-butyric acid methyl ester (909016-30-4)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; hexane; at -78 ℃;

DOI:10.1246/cl.1998.85

Reference yield:

(S)-2-(2-Benzyloxy-1,1-dimethyl-ethyl)-oxirane (111080-21-8) → 4-[(4S,6R)-6-(2-Benzyloxy-1,1-dimethyl-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-3-hydroxy-2-methyl-butyric acid methyl ester (909016-30-4)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 92 percent / n-BuLi / tetrahydrofuran; hexane / -78 - -30 °C

2.1: (CF₃CO₂)2IPh / methanol / 0.75 h / 0 °C

2.2: 77 percent / aq. AcOH / tetrahydrofuran / 0.25 h / 20 °C

3.1: 86 percent / Me₄NBH(OAc)3; AcOH / acetonitrile / -40 - -30 °C

4.1: 97 percent / (+/-)-camphorsulfonic acid / acetone / 19 h / 20 °C

5.1: OsO₄; N-methylmorpholine-N-oxide; H₂O / 2-methyl-propan-2-ol; acetone / 2 h / 20 °C

6.1: 1.53 g / aq. NaIO₄; N-methylmorpholine-N-oxide / 2-methyl-propan-2-ol; acetone / 0.5 h / 20 °C

7.1: 88 percent / Et₂Zn; RhCl(PPh₃)3 / tetrahydrofuran; hexane / 0.58 h / 0 °C

With sodium periodate; osmium(VIII) oxide; n-butyllithium; RhCl(PPh₃)3; camphor-10-sulfonic acid; water; diethylzinc; acetic acid; 4-methylmorpholine N-oxide; bis-[(trifluoroacetoxy)iodo]benzene; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; methanol; hexane; acetone; acetonitrile; tert-butyl alcohol;

DOI:10.1016/j.tet.2006.05.077

upstream raw materials:

propanoic acid methyl ester

[(4R,6R)-6-(2-Benzyloxy-1,1-dimethyl-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-acetaldehyde

Methyl 2-bromopropionate

(S)-2-(2-Benzyloxy-1,1-dimethyl-ethyl)-oxirane

Downstream raw materials:

2-[(2S,4R,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-((3E,7E)-(R)-2-hydroxy-1,1,4-trimethyl-6-triethylsilanyloxy-10-trimethylsilanyl-deca-3,7-dien-9-ynyl)-2-methoxy-tetrahydro-pyran-2-yl]-propionic acid methyl ester

2-[(2S,4R,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-((3E,7E)-(R)-2,6-dihydroxy-1,1,4-trimethyl-9-trityloxy-nona-3,7-dienyl)-2-methoxy-tetrahydro-pyran-2-yl]-propionic acid

2-[(2S,4R,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-((3E,7E)-(R)-2-hydroxy-1,1,4-trimethyl-6-triethylsilanyloxy-9-trityloxy-nona-3,7-dienyl)-2-methoxy-tetrahydro-pyran-2-yl]-propionic acid methyl ester

2-[(2S,4R,6R)-6-(2-Benzyloxy-1,1-dimethyl-ethyl)-4-hydroxy-2-methoxy-tetrahydro-pyran-2-yl]-propionic acid methyl ester