benzylamino-(3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-acetic acid methyl ester

Base Information

• Chemical Name: benzylamino-(3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-acetic acid methyl ester
• CAS No.: 934349-44-7
• Molecular Formula: C₄₄H₄₇NO₇
• Molecular Weight: 701.86
• Mol file: 934349-44-7.mol

Synonyms:benzylamino-(3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-acetic acid methyl ester

Chemical Property of benzylamino-(3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-acetic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzylamino-(3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-acetic acid methyl ester

There total 6 articles about benzylamino-(3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-acetic acid methyl ester 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: 56.0%

trifluoromethanesulfonyloxy-(3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-acetic acid methyl ester (934349-43-6) + benzylamine (100-46-9) → benzylamino-(3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-acetic acid methyl ester (934349-44-7)

Guidance literature:

In 1,2-dichloro-ethane; at 50 ℃; for 24h;

DOI:10.1055/s-2007-968002

Reference yield:

(1R)-2,3,4,6-tetra-O-benzyl-3'(S)-carboxymethyl-spiro[1,5-anhydro-D-glucitol-1,2'-oxirane] (883143-12-2) → benzylamino-(3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-acetic acid methyl ester (934349-44-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: tributyltin hydride; trimethylsilyltrifluoromethanesulfonate / CH₂Cl₂ / 0.5 h / 0 °C

1.2: 100 percent / trifluoroacetic acid / tetrahydrofuran; CH₂Cl₂ / 2 h

2.1: 100 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

3.1: 56 percent / 1,2-dichloro-ethane / 24 h / 50 °C

With pyridine; trimethylsilyl trifluoromethanesulfonate; tri-n-butyl-tin hydride; In dichloromethane; 1,2-dichloro-ethane;

DOI:10.1055/s-2007-968002

Reference yield:

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one (13096-62-3) → benzylamino-(3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-acetic acid methyl ester (934349-44-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 80 percent / LiHMDS / tetrahydrofuran / 2 h / -78 - 20 °C

2.1: tributyltin hydride; trimethylsilyltrifluoromethanesulfonate / CH₂Cl₂ / 0.5 h / 0 °C

2.2: 100 percent / trifluoroacetic acid / tetrahydrofuran; CH₂Cl₂ / 2 h

3.1: 100 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

4.1: 56 percent / 1,2-dichloro-ethane / 24 h / 50 °C

With pyridine; trimethylsilyl trifluoromethanesulfonate; tri-n-butyl-tin hydride; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane;

DOI:10.1055/s-2007-968002

upstream raw materials:

trifluoromethanesulfonyloxy-(3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-acetic acid methyl ester

benzylamine

(1R)-2,3,4,6-tetra-O-benzyl-3'(S)-carboxymethyl-spiro[1,5-anhydro-D-glucitol-1,2'-oxirane]

(2S)-methyl 2-hydroxy-2-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-ethanoate

Downstream raw materials:

C₄₁H₅₆N₄O₁₃

C₄₁H₅₇N₅O₁₂

C₅₁H₅₉N₅O₁₂