ethyl [(2R,4S,5R)-5-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-4-{[(tert-butyl)(dimethyl)silyl]oxy}tetrahydrofuran-2-yl]acetate

Base Information

• Chemical Name: ethyl [(2R,4S,5R)-5-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-4-{[(tert-butyl)(dimethyl)silyl]oxy}tetrahydrofuran-2-yl]acetate
• CAS No.: 634178-89-5
• Molecular Formula: C₃₆H₄₈O₇Si
• Molecular Weight: 620.858
• Mol file: 634178-89-5.mol

Synonyms:ethyl [(2R,4S,5R)-5-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-4-{[(tert-butyl)(dimethyl)silyl]oxy}tetrahydrofuran-2-yl]acetate

Chemical Property of ethyl [(2R,4S,5R)-5-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-4-{[(tert-butyl)(dimethyl)silyl]oxy}tetrahydrofuran-2-yl]acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl [(2R,4S,5R)-5-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-4-{[(tert-butyl)(dimethyl)silyl]oxy}tetrahydrofuran-2-yl]acetate

There total 2 articles about ethyl [(2R,4S,5R)-5-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-4-{[(tert-butyl)(dimethyl)silyl]oxy}tetrahydrofuran-2-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: 85.0%

tert-butyldimethylsilyl chloride (18162-48-6) + ethyl [2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl]acetate (197784-38-6) → ethyl [(2R,4S,5R)-5-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-4-{[(tert-butyl)(dimethyl)silyl]oxy}tetrahydrofuran-2-yl]acetate (634178-89-5)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 16h;

DOI:10.1016/S0968-0896(03)00229-3

Reference yield:

4,4'-dimethoxytrityl chloride (40615-36-9) → ethyl [(2R,4S,5R)-5-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-4-{[(tert-butyl)(dimethyl)silyl]oxy}tetrahydrofuran-2-yl]acetate (634178-89-5)

Guidance literature:

1: Substitution / 1: Condensation / 2: Substitution;

DOI:10.1080/07328319908044686

Reference yield: 90.0%

3-Iodoaniline (626-01-7) + ethyl [(2R,4S,5R)-5-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-4-{[(tert-butyl)(dimethyl)silyl]oxy}tetrahydrofuran-2-yl]acetate (634178-89-5) → 2-[5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-N-(3-iodo-phenyl)-acetamide (634178-90-8)

Guidance literature:

With 4 A molecular sieve; trimethylaluminum; In toluene; at 20 ℃; for 2h;

DOI:10.1016/S0968-0896(03)00229-3

upstream raw materials:

tert-butyldimethylsilyl chloride

ethyl [2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl]acetate

4,4'-dimethoxytrityl chloride

Downstream raw materials:

2-[5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-N-(3-iodo-phenyl)-acetamide

{5-[3-(2-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-acetylamino)-phenyl]-thiazol-2-yl}-methyl-carbamic acid tert-butyl ester

[5-(3-{2-[5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-acetylamino}-phenyl)-thiazol-2-yl]-methyl-carbamic acid tert-butyl ester

2-[(2R,4S,5R)-5-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-4-{[(tert-butyl)(dimethyl)silyl]-oxy}tetrahydrofuran-2-yl]-N-{2-[2-(2-hydroxyethoxy)ethoxy]ethyl}acetamide