methyl [3,7-anhydro-2-deoxy-3-C-(aminomethyl-(N-L-Phe-N^α(Fmoc)amide))-D-glycero-L-manno-oct]onate

Base Information

• Chemical Name: methyl [3,7-anhydro-2-deoxy-3-C-(aminomethyl-(N-L-Phe-N^α(Fmoc)amide))-D-glycero-L-manno-oct]onate
• CAS No.: 903882-03-1
• Molecular Formula: C₃₄H₃₈N₂O₁₀
• Molecular Weight: 634.683

Synonyms:methyl [3,7-anhydro-2-deoxy-3-C-(aminomethyl-(N-L-Phe-N^α(Fmoc)amide))-D-glycero-L-manno-oct]onate

Chemical Property of methyl [3,7-anhydro-2-deoxy-3-C-(aminomethyl-(N-L-Phe-N^α(Fmoc)amide))-D-glycero-L-manno-oct]onate

Chemical Property:

Purity/Quality:

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Technology Process of methyl [3,7-anhydro-2-deoxy-3-C-(aminomethyl-(N-L-Phe-N^α(Fmoc)amide))-D-glycero-L-manno-oct]onate

There total 5 articles about methyl [3,7-anhydro-2-deoxy-3-C-(aminomethyl-(N-L-Phe-N^α(Fmoc)amide))-D-glycero-L-manno-oct]onate 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:

2,3,4,6-tetra-O-benzyl-D-galactonolactone (82598-84-3) → methyl [3,7-anhydro-2-deoxy-3-C-(aminomethyl-(N-L-Phe-Nα(Fmoc)amide))-D-glycero-L-manno-oct]onate (903882-03-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 95 percent / tetrahydrofuran / 1 h / -78 - 20 °C

2: trifluoroacetic acid / CH₂Cl₂ / 2 h / 0 °C

3: 766 mg / cesium carbonate / dimethylformamide / 4 h / 20 °C

4: 75 percent / trimethylsilyl trifluoromethanesulfonate / acetonitrile / 36 h / 0 - 20 °C

5: 90 percent / hydrogen; hydrochloric acid / Pd(OH)2/C / methanol / 60 h

6: 65 percent / sodium bicarbonate / H₂O; acetone / 13 h

With hydrogenchloride; trimethylsilyl trifluoromethanesulfonate; hydrogen; sodium hydrogencarbonate; caesium carbonate; trifluoroacetic acid; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile;

DOI:10.1016/j.carres.2006.03.006

Reference yield:

methyl (3,7-anhydro-4,5,6,8-tetra-O-benzyl-3-cyano-2-deoxy-D-glycero-L-manno-oct)onate (400888-52-0) → methyl [3,7-anhydro-2-deoxy-3-C-(aminomethyl-(N-L-Phe-Nα(Fmoc)amide))-D-glycero-L-manno-oct]onate (903882-03-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / hydrogen; hydrochloric acid / Pd(OH)2/C / methanol / 60 h

2: 65 percent / sodium bicarbonate / H₂O; acetone / 13 h

With hydrogenchloride; hydrogen; sodium hydrogencarbonate; palladium dihydroxide; In methanol; water; acetone;

DOI:10.1016/j.carres.2006.03.006

Reference yield:

methyl (4,5,6,8-tetra-O-benzyl-2-deoxy-α-D-galacto-3-octulopyranosid)onate (400888-43-9) → methyl [3,7-anhydro-2-deoxy-3-C-(aminomethyl-(N-L-Phe-Nα(Fmoc)amide))-D-glycero-L-manno-oct]onate (903882-03-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 75 percent / trimethylsilyl trifluoromethanesulfonate / acetonitrile / 36 h / 0 - 20 °C

2: 90 percent / hydrogen; hydrochloric acid / Pd(OH)2/C / methanol / 60 h

3: 65 percent / sodium bicarbonate / H₂O; acetone / 13 h

With hydrogenchloride; trimethylsilyl trifluoromethanesulfonate; hydrogen; sodium hydrogencarbonate; palladium dihydroxide; In methanol; water; acetone; acetonitrile;

DOI:10.1016/j.carres.2006.03.006

upstream raw materials:

2,3,4,6-tetra-O-benzyl-D-galactonolactone

methyl (4,5,6,8-tetra-O-benzyl-2-deoxy-α-D-galacto-3-octulopyranosid)onate

methyl (3,7-anhydro-4,5,6,8-tetra-O-benzyl-3-cyano-2-deoxy-D-glycero-L-manno-oct)onate

((2S,3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-hydroxy-tetrahydro-pyran-2-yl)-acetic acid tert-butyl ester

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