methyl N-{[(3R,5S,8R,9S,10S,13S,14S)-3-hydroxy-10,13-dimethylhexadecahydrospiro[cyclopenta[a]phenanthrene-17,2'-[1,3]dioxolan]-3-yl]methyl}-L-phenylalaninate

Base Information

• Chemical Name: methyl N-{[(3R,5S,8R,9S,10S,13S,14S)-3-hydroxy-10,13-dimethylhexadecahydrospiro[cyclopenta[a]phenanthrene-17,2'-[1,3]dioxolan]-3-yl]methyl}-L-phenylalaninate
• CAS No.: 1401938-70-2
• Molecular Formula: C₃₂H₄₇NO₅
• Molecular Weight: 525.729
• Mol file: 1401938-70-2.mol

Synonyms:methyl N-{[(3R,5S,8R,9S,10S,13S,14S)-3-hydroxy-10,13-dimethylhexadecahydrospiro[cyclopenta[a]phenanthrene-17,2'-[1,3]dioxolan]-3-yl]methyl}-L-phenylalaninate

Chemical Property of methyl N-{[(3R,5S,8R,9S,10S,13S,14S)-3-hydroxy-10,13-dimethylhexadecahydrospiro[cyclopenta[a]phenanthrene-17,2'-[1,3]dioxolan]-3-yl]methyl}-L-phenylalaninate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl N-{[(3R,5S,8R,9S,10S,13S,14S)-3-hydroxy-10,13-dimethylhexadecahydrospiro[cyclopenta[a]phenanthrene-17,2'-[1,3]dioxolan]-3-yl]methyl}-L-phenylalaninate

There total 7 articles about methyl N-{[(3R,5S,8R,9S,10S,13S,14S)-3-hydroxy-10,13-dimethylhexadecahydrospiro[cyclopenta[a]phenanthrene-17,2'-[1,3]dioxolan]-3-yl]methyl}-L-phenylalaninate 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: 77.0%

methyl (2S)-2-amino-3-phenylpropanoate (2577-90-4) + spiro-3(R)-oxirane-5α-androstane-17-dioxolane (400604-16-2) → methyl N-{[(3R,5S,8R,9S,10S,13S,14S)-3-hydroxy-10,13-dimethylhexadecahydrospiro[cyclopenta[a]phenanthrene-17,2'-[1,3]dioxolan]-3-yl]methyl}-L-phenylalaninate (1401938-70-2)

Guidance literature:

In methanol; at 90 ℃; for 21h; Schlenk technique; Inert atmosphere;

DOI:10.1016/j.bmc.2015.07.049

Reference yield: 77.0%

→ methyl N-{[(3R,5S,8R,9S,10S,13S,14S)-3-hydroxy-10,13-dimethylhexadecahydrospiro[cyclopenta[a]phenanthrene-17,2'-[1,3]dioxolan]-3-yl]methyl}-L-phenylalaninate (1401938-70-2)

Guidance literature:

Reference yield:

cis-androsterone (53-41-8) → methyl N-{[(3R,5S,8R,9S,10S,13S,14S)-3-hydroxy-10,13-dimethylhexadecahydrospiro[cyclopenta[a]phenanthrene-17,2'-[1,3]dioxolan]-3-yl]methyl}-L-phenylalaninate (1401938-70-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: toluene-4-sulfonic acid / toluene / Reflux

2.1: 4-methylmorpholine N-oxide; tetrapropylammonium perruthennate / dichloromethane / 3 h / 20 °C / Molecular sieve

2.2: 20 °C

3.1: methanol / 90 °C

With tetrapropylammonium perruthennate; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; In methanol; dichloromethane; toluene;

DOI:10.1016/j.bmcl.2013.09.072

upstream raw materials:

methyl (2S)-2-amino-3-phenylpropanoate

spiro-3(R)-oxirane-5α-androstane-17-dioxolane

cis-androsterone

(3α,5α)-3-hydroxyandrostan-17-one 1,2-ethanediyl acetal

Downstream raw materials:

(3'R,5'S,5S,8'R,9'S,10'S,13'S,14'S)-5-benzyl-10',13'-dimethyltetradecahydro-2'H,6H-dispiro[1,3-dioxolane-2,17'-cyclopenta[a]phenanthrene-3',2-[1,4]oxazinan]-6-one

(3R,5S,5'S,8R,9S,10S,13S,14S)-5'-benzyl-10,13-dimethyltetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione

(3'R,5'S,5S,8'R,9'S,10'S,13'S,14'S)-4,5-dibenzyl-10',13'-dimethyltetradecahydro-2'H,6H-dispiro[1,3-dioxolane-2,17'-cyclopenta[a]phenanthrene-3',2-[1,4]oxazinan]-6-one

(3R,5S,5'S,8R,9S,10S,13S,14S)-4',5'-dibenzyl-10,13-dimethyltetradecahydro-6'H-spiro[cyclopenta[a]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2H)-dione