HO-D-Hpla(TIPS)-D-Leu-O-t-Bu

Base Information

• Chemical Name: HO-D-Hpla(TIPS)-D-Leu-O-t-Bu
• CAS No.: 611182-65-1
• Molecular Formula: C₂₈H₄₉NO₅Si
• Molecular Weight: 507.786
• Mol file: 611182-65-1.mol

Synonyms:HO-D-Hpla(TIPS)-D-Leu-O-t-Bu

Chemical Property of HO-D-Hpla(TIPS)-D-Leu-O-t-Bu

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of HO-D-Hpla(TIPS)-D-Leu-O-t-Bu

There total 1 articles about HO-D-Hpla(TIPS)-D-Leu-O-t-Bu 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%

tert-butyl (R)-2-amino-4-methylpent-4-enoate (339304-38-0) + (2R,3S)-3-[4-(triisopropylsilanyloxy)phenyl]oxirane-2-carboperoxoic acid tert-butyl ester (611182-64-0) → leucine tert-butylester (17389-05-8) + D-leucine t-butyl ester (67617-35-0) + 2-[2-hydroxy-3-(4-triisopropylsilanyloxy-phenyl)-propionylamino]-4-methyl-pentanoic acid tert-butyl ester + HO-D-Hpla(TIPS)-D-Leu-O-t-Bu (611182-65-1)

Guidance literature:

tert-butyl (R)-2-amino-4-methylpent-4-enoate; (2R,3S)-3-[4-(triisopropylsilanyloxy)phenyl]oxirane-2-carboperoxoic acid tert-butyl ester; In tetrahydrofuran; at 20 ℃; for 24h;

With palladium on activated charcoal; hydrogen; In tetrahydrofuran; for 24h;

DOI:10.1021/ja037290e

Reference yield:

triisopropylsilyl trifluoromethanesulfonate (80522-42-5) + HO-D-Hpla(TIPS)-D-Leu-O-t-Bu (611182-65-1) → (R)-4-Methyl-2-[(R)-2-triisopropylsilanyloxy-3-(4-triisopropylsilanyloxy-phenyl)-propionylamino]-pentanoic acid tert-butyl ester

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; at 10 ℃; for 0.5h;

DOI:10.1021/ja037290e

Reference yield:

HO-D-Hpla(TIPS)-D-Leu-O-t-Bu (611182-65-1) → HO-D-Hpla-D-Leu-L-Choi-L-Argol

Guidance literature:

Multi-step reaction with 5 steps

1.1: i-Pr₂NEt / dioxane / 0.5 h / 10 °C

2.1: TMSOTf / dioxane / 1 h / Heating

3.1: 39.5 mg / HATU; i-Pr₂NEt / dimethylformamide / 18 h / 20 °C

4.1: 54 percent / LiBH₄ / tetrahydrofuran / 1 h / 4 °C

5.1: HF*Py / tetrahydrofuran / 24 h / 20 °C

5.2: 7.3 g / Pd/C; H₂ / ethanol; tetrahydrofuran / 1 h / 760 Torr

With lithium borohydride; trimethylsilyl trifluoromethanesulfonate; pyridine hydrogenfluoride; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In tetrahydrofuran; 1,4-dioxane; N,N-dimethyl-formamide;

DOI:10.1021/ja037290e

upstream raw materials:

tert-butyl (R)-2-amino-4-methylpent-4-enoate

(2R,3S)-3-[4-(triisopropylsilanyloxy)phenyl]oxirane-2-carboperoxoic acid tert-butyl ester

Downstream raw materials:

(R)-4-Methyl-2-[(R)-2-triisopropylsilanyloxy-3-(4-triisopropylsilanyloxy-phenyl)-propionylamino]-pentanoic acid

TIPSO-D-Hpla(TIPS)-D-Leu-L-Choi(TIPS)-L-Argol(δ,ω'-di-Cbz)

TIPSO-D-Hpla(TIPS)-D-Leu-L-Choi(TIPS)-L-Arg(δ,ω'-di-Cbz)-OMe

Refernces