(S)-1-(4-Methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-4-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-but-3-ynylamine

Base Information

• Chemical Name: (S)-1-(4-Methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-4-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-but-3-ynylamine
• CAS No.: 402578-82-9
• Molecular Formula: C₄₄H₄₉NO₈
• Molecular Weight: 719.875
• Mol file: 402578-82-9.mol

Synonyms:(S)-1-(4-Methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-4-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-but-3-ynylamine

Chemical Property of (S)-1-(4-Methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-4-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-but-3-ynylamine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-1-(4-Methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-4-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-but-3-ynylamine

There total 5 articles about (S)-1-(4-Methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-4-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-but-3-ynylamine 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:

(3-methyloxetan-3-yl)methyl 4-methylbenzenesulfonate (99314-44-0) → (S)-1-(4-Methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-4-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-but-3-ynylamine (402578-82-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 45 percent / NaI / dimethylformamide / 48 h / 20 °C

2: 78 percent / BF₃*OEt₂ / CH₂Cl₂ / 4 h / 20 °C

3: 98 percent / PPh₃; DEAD / 1 h / 0 °C

4: 82 percent / tetrahydrofuran / 0 - 20 °C

5: K₂CO₃; PhSH; DMSO / acetonitrile / 4 h / 50 °C

With boron trifluoride diethyl etherate; potassium carbonate; dimethyl sulfoxide; thiophenol; triphenylphosphine; sodium iodide; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0040-4039(01)01886-X

Reference yield:

N-[(S)-1-(4-Methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-4-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-but-3-ynyl]-2-nitro-benzenesulfonamide (402578-78-3) → (S)-1-(4-Methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-4-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-but-3-ynylamine (402578-82-9)

Guidance literature:

With potassium carbonate; dimethyl sulfoxide; thiophenol; In acetonitrile; at 50 ℃; for 4h;

DOI:10.1016/S0040-4039(01)01886-X

Reference yield:

1-[(S)-1-(2-nitrobenzenesulfonyl)-aziridin-2-yl]-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane (402578-49-8) → (S)-1-(4-Methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-4-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-but-3-ynylamine (402578-82-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / tetrahydrofuran / 0 - 20 °C

2: K₂CO₃; PhSH; DMSO / acetonitrile / 4 h / 50 °C

With potassium carbonate; dimethyl sulfoxide; thiophenol; In tetrahydrofuran; acetonitrile;

DOI:10.1016/S0040-4039(01)01886-X

upstream raw materials:

N-[(S)-1-(4-Methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-4-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-but-3-ynyl]-2-nitro-benzenesulfonamide

(3-methyloxetan-3-yl)methyl 4-methylbenzenesulfonate

1-[(S)-1-(2-nitrobenzenesulfonyl)-aziridin-2-yl]-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane

N-[2-hydroxy-1-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-ethyl]-2-nitro-benzenesulfonamide

Downstream raw materials:

(S)-2-Amino-5-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-pent-4-ynoic acid

6,10-anhydro-7,8,9,11-tetra-O-benzyl-2,3,4,5-tetradeoxy-2-(tert-butoxycarbonylamino)-D-threo-L-galacto-undeconic acid

(S)-2-tert-Butoxycarbonylamino-5-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-pent-4-ynoic acid