(2S,3S,1'S,2'R,3'R)-1-(tert-Butoxycarbonyl)-2-<3'-benzyloxycarbonylamine-4'-(tert-butyldimethylsilyloxy)-1'-hydroxy-2'-phenylsulfonylbutyl>-3-(methoxymethoxy)pyrrolidine

Base Information

• Chemical Name: (2S,3S,1'S,2'R,3'R)-1-(tert-Butoxycarbonyl)-2-<3'-benzyloxycarbonylamine-4'-(tert-butyldimethylsilyloxy)-1'-hydroxy-2'-phenylsulfonylbutyl>-3-(methoxymethoxy)pyrrolidine
• CAS No.: 153277-26-0
• Molecular Formula: C₃₅H₅₄N₂O₁₀SSi
• Molecular Weight: 722.973
• Mol file: 153277-26-0.mol

Synonyms:(2S,3S,1'S,2'R,3'R)-1-(tert-Butoxycarbonyl)-2-<3'-benzyloxycarbonylamine-4'-(tert-butyldimethylsilyloxy)-1'-hydroxy-2'-phenylsulfonylbutyl>-3-(methoxymethoxy)pyrrolidine

Chemical Property of (2S,3S,1'S,2'R,3'R)-1-(tert-Butoxycarbonyl)-2-<3'-benzyloxycarbonylamine-4'-(tert-butyldimethylsilyloxy)-1'-hydroxy-2'-phenylsulfonylbutyl>-3-(methoxymethoxy)pyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,1'S,2'R,3'R)-1-(tert-Butoxycarbonyl)-2-<3'-benzyloxycarbonylamine-4'-(tert-butyldimethylsilyloxy)-1'-hydroxy-2'-phenylsulfonylbutyl>-3-(methoxymethoxy)pyrrolidine

There total 17 articles about (2S,3S,1'S,2'R,3'R)-1-(tert-Butoxycarbonyl)-2-<3'-benzyloxycarbonylamine-4'-(tert-butyldimethylsilyloxy)-1'-hydroxy-2'-phenylsulfonylbutyl>-3-(methoxymethoxy)pyrrolidine 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: 60.0%

(2R,3S)-1-(tert-Butoxycarbonyl)-3-(methoxymethoxy)pyrrolidine-2-carbaldehyde (153277-25-9) + (R)-2-Benzyloxycarbonylamino-1-(tert-butyldimethylsilyloxy)-3-phenylsulfonylpropane (153277-21-5) → (2S,3S,1'S,2'R,3'R)-1-(tert-Butoxycarbonyl)-2-<3'-benzyloxycarbonylamine-4'-(tert-butyldimethylsilyloxy)-1'-hydroxy-2'-phenylsulfonylbutyl>-3-(methoxymethoxy)pyrrolidine (153277-26-0)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; 1.) -78 deg C to 0 deg C, 1 h, 2.) -78 deg C to 0 deg C, 4 h;

Reference yield:

N-benzyloxycarbonyl-L-serine methyl ester (1676-81-9) → (2S,3S,1'S,2'R,3'R)-1-(tert-Butoxycarbonyl)-2-<3'-benzyloxycarbonylamine-4'-(tert-butyldimethylsilyloxy)-1'-hydroxy-2'-phenylsulfonylbutyl>-3-(methoxymethoxy)pyrrolidine (153277-26-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 78 percent / DMAP, pyridine / CH₂Cl₂ / 16 h / -18 °C

2: 98 percent / NaH / dimethylformamide / 1.) 10 min, 2.) 20 deg C, 16 h

3: 97 percent / NaBH₄ / methanol / 5 h / 20 °C

4: 92 percent / DMAP, Et₃N / CH₂Cl₂ / 16 h / 20 °C

5: 87 percent / MCPBA / CH₂Cl₂ / 1.) ice-cooling, 0.5 h, 2.) 20 deg C, 2 h

6: 60 percent / BuLi / tetrahydrofuran; hexane / 1.) -78 deg C to 0 deg C, 1 h, 2.) -78 deg C to 0 deg C, 4 h

With pyridine; dmap; sodium tetrahydroborate; n-butyllithium; sodium hydride; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide;

Reference yield:

(2S,3S)-1-(tert-Butoxycarbonyl)-3-(methoxymethoxy)pyrrolidine-2-methanol (153277-24-8) → (2S,3S,1'S,2'R,3'R)-1-(tert-Butoxycarbonyl)-2-<3'-benzyloxycarbonylamine-4'-(tert-butyldimethylsilyloxy)-1'-hydroxy-2'-phenylsulfonylbutyl>-3-(methoxymethoxy)pyrrolidine (153277-26-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 79 percent / TPAP, N-methylmorpholine N-oxide, molecular sieves / CH₂Cl₂; acetonitrile / 18 h / Ambient temperature

2: 60 percent / BuLi / tetrahydrofuran; hexane / 1.) -78 deg C to 0 deg C, 1 h, 2.) -78 deg C to 0 deg C, 4 h

With n-butyllithium; molecular sieve; tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide; In tetrahydrofuran; hexane; dichloromethane; acetonitrile;

upstream raw materials:

(2R,3S)-1-(tert-Butoxycarbonyl)-3-(methoxymethoxy)pyrrolidine-2-carbaldehyde

(R)-2-Benzyloxycarbonylamino-1-(tert-butyldimethylsilyloxy)-3-phenylsulfonylpropane

N-benzyloxycarbonyl-L-serine methyl ester

Methyl 1-(tert-butoxycarbonyl)-3-oxopyrrolidine-2-carboxylate

Downstream raw materials:

(2S,3S)-2-[(E)-(S)-3-Benzyloxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-but-1-enyl]-3-methoxymethoxy-pyrrolidine-1-carboxylic acid tert-butyl ester

(1S,6S,8aS)-1-acetoxy-6-aminooctahydroindolizidine

O-Deacetyl-N-(benzyloxycarbonyl)slaframine

((1S,6S,8aS)-1-Methoxymethoxy-octahydro-indolizin-6-yl)-carbamic acid benzyl ester