2-tert-butoxycarbonylamino-3-[4-(2,2-di-tert-butyl-8-triisopropylsilanyloxy-4,4a,8,8a-tetrahydro-1,3,5-trioxa-2-sila-naphthalen-6-yl)-phenyl]-propionic acid tert-butyl ester

Base Information

• Chemical Name: 2-tert-butoxycarbonylamino-3-[4-(2,2-di-tert-butyl-8-triisopropylsilanyloxy-4,4a,8,8a-tetrahydro-1,3,5-trioxa-2-sila-naphthalen-6-yl)-phenyl]-propionic acid tert-butyl ester
• CAS No.: 885019-64-7
• Molecular Formula: C₄₁H₇₁NO₈Si₂
• Molecular Weight: 762.188
• Mol file: 885019-64-7.mol

Synonyms:2-tert-butoxycarbonylamino-3-[4-(2,2-di-tert-butyl-8-triisopropylsilanyloxy-4,4a,8,8a-tetrahydro-1,3,5-trioxa-2-sila-naphthalen-6-yl)-phenyl]-propionic acid tert-butyl ester

Chemical Property of 2-tert-butoxycarbonylamino-3-[4-(2,2-di-tert-butyl-8-triisopropylsilanyloxy-4,4a,8,8a-tetrahydro-1,3,5-trioxa-2-sila-naphthalen-6-yl)-phenyl]-propionic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-tert-butoxycarbonylamino-3-[4-(2,2-di-tert-butyl-8-triisopropylsilanyloxy-4,4a,8,8a-tetrahydro-1,3,5-trioxa-2-sila-naphthalen-6-yl)-phenyl]-propionic acid tert-butyl ester

There total 1 articles about 2-tert-butoxycarbonylamino-3-[4-(2,2-di-tert-butyl-8-triisopropylsilanyloxy-4,4a,8,8a-tetrahydro-1,3,5-trioxa-2-sila-naphthalen-6-yl)-phenyl]-propionic acid tert-butyl 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: 90.0%

1,5-anhydro-2-deoxy-4,6-O-bis(tert-butylsilylidene)-3-O-triisopropylsilyl-D-arabino-hex-1-enitol (262266-33-1) + N-[(1,1-dimethylethoxy)carbonyl]-4-iodo-L-phenylalanine 1,1-dimethylethyl ester (217326-89-1) → 2-tert-butoxycarbonylamino-3-[4-(2,2-di-tert-butyl-8-triisopropylsilanyloxy-4,4a,8,8a-tetrahydro-1,3,5-trioxa-2-sila-naphthalen-6-yl)-phenyl]-propionic acid tert-butyl ester (885019-64-7) + (4aR,8R,8aR,4'aR,8'R,8'aR)-2,2,2',2'-Tetra-tert-butyl-8,8'-bis-triisopropylsilanyloxy-4,4a,8,8a,4',4'a,8',8'a-octahydro-[6,6']bi[1,3,5-trioxa-2-sila-naphthalenyl]

Guidance literature:

1,5-anhydro-2-deoxy-4,6-O-bis(tert-butylsilylidene)-3-O-triisopropylsilyl-D-arabino-hex-1-enitol; With tert.-butyl lithium; In tetrahydrofuran; pentane; at -78 - 0 ℃;

With zinc(II) chloride; In tetrahydrofuran; pentane; at 20 ℃; for 1h;

N-[(1,1-dimethylethoxy)carbonyl]-4-iodo-L-phenylalanine 1,1-dimethylethyl ester; With tris-(o-tolyl)phosphine; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In tetrahydrofuran; pentane; at 20 ℃;

DOI:10.1002/ejoc.200500690

Reference yield:

2-tert-butoxycarbonylamino-3-[4-(2,2-di-tert-butyl-8-triisopropylsilanyloxy-4,4a,8,8a-tetrahydro-1,3,5-trioxa-2-sila-naphthalen-6-yl)-phenyl]-propionic acid tert-butyl ester (885019-64-7) → (S)-2-tert-Butoxycarbonylamino-3-[4-((4aR,6S,7S,8R,8aR)-2,2-di-tert-butyl-7-hydroxy-8-triisopropylsilanyloxy-hexahydro-1,3,5-trioxa-2-sila-naphthalen-6-yl)-phenyl]-propionic acid tert-butyl ester

Guidance literature:

2-tert-butoxycarbonylamino-3-[4-(2,2-di-tert-butyl-8-triisopropylsilanyloxy-4,4a,8,8a-tetrahydro-1,3,5-trioxa-2-sila-naphthalen-6-yl)-phenyl]-propionic acid tert-butyl ester; With borane-THF; In tetrahydrofuran; at 0 ℃;

With sodium hydroxide; dihydrogen peroxide; In tetrahydrofuran; water; at 0 - 20 ℃;

DOI:10.1002/ejoc.200500690

Reference yield:

2-tert-butoxycarbonylamino-3-[4-(2,2-di-tert-butyl-8-triisopropylsilanyloxy-4,4a,8,8a-tetrahydro-1,3,5-trioxa-2-sila-naphthalen-6-yl)-phenyl]-propionic acid tert-butyl ester (885019-64-7) → (S)-2-Amino-3-[4-((2S,3S,4R,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl)-phenyl]-propionic acid

Guidance literature:

Multi-step reaction with 5 steps

1.1: 86 percent / nBu₄NF*3H₂O / tetrahydrofuran / 22 h / 0 - 20 °C

2.1: 0.24 g / pyridine; DMAP / 20 °C

3.1: BH₃*THF / tetrahydrofuran / 4 h / 0 °C

3.2: NaOH; H₂O₂ / tetrahydrofuran; H₂O / 2.5 h / 0 - 20 °C

4.1: 0.215 g / pyridine; DMAP / 20 °C

5.1: TFA / CH₂Cl₂ / 5 h / 20 °C

With pyridine; dmap; borane-THF; tetrabutyl ammonium fluoride; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1002/ejoc.200500690

upstream raw materials:

1,5-anhydro-2-deoxy-4,6-O-bis(tert-butylsilylidene)-3-O-triisopropylsilyl-D-arabino-hex-1-enitol

N-[(1,1-dimethylethoxy)carbonyl]-4-iodo-L-phenylalanine 1,1-dimethylethyl ester

Downstream raw materials:

N-[(1,1-dimethylethoxy)carbonyl]-4-(3,4,6-tri-O-acetyl-1,2-dideoxy-D-arabino-hexenopyranosyl)-L-phenylalanine 1,1-dimethylethyl ester

N-[(1,1-dimethylethoxy)carbonyl]-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-L-phenylalanine 1,1-dimethylethyl ester