(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

Base Information

• Chemical Name: (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
• CAS No.: 402578-87-4
• Molecular Formula: C₄₄H₄₉NO₉
• Molecular Weight: 735.874
• Mol file: 402578-87-4.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 2 articles about (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 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:

(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) → (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 (402578-87-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: TFA / CH₂Cl₂; H₂O / 3 h / 20 °C

1.2: Cs₂CO₃ / dioxane; methanol; H₂O / 16 h / 20 °C

2.1: 92 percent / Na₂CO₃ / dioxane; H₂O / 5 h / 20 °C

With sodium carbonate; trifluoroacetic acid; In 1,4-dioxane; dichloromethane; water;

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)-2-tert-Butoxycarbonylamino-5-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-pent-4-ynoic acid (402578-87-4)

Guidance literature:

Multi-step reaction with 3 steps

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

2.1: TFA / CH₂Cl₂; H₂O / 3 h / 20 °C

2.2: Cs₂CO₃ / dioxane; methanol; H₂O / 16 h / 20 °C

3.1: 92 percent / Na₂CO₃ / dioxane; H₂O / 5 h / 20 °C

With sodium carbonate; potassium carbonate; dimethyl sulfoxide; thiophenol; trifluoroacetic acid; In 1,4-dioxane; dichloromethane; water; acetonitrile;

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

Reference yield:

(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 (402578-87-4) → 6,10-anhydro-7,8,9,11-tetra-O-benzyl-2,3,4,5-tetradeoxy-2-(tert-butoxycarbonylamino)-D-threo-L-galacto-undeconic acid (213828-80-9)

Guidance literature:

With hydrogen; palladium on activated charcoal; In 1,4-dioxane; ethanol; water; at 20 ℃; for 4h;

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

upstream raw materials:

(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

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

Downstream raw materials:

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