O-(2-acetamido-3,4-di-O-benzyl-2-deoxy-α-D-galactopyranosyl)-N-(tert-butyloxycarbonyl)-L-serine tert-butyl ester

Base Information

• Chemical Name: O-(2-acetamido-3,4-di-O-benzyl-2-deoxy-α-D-galactopyranosyl)-N-(tert-butyloxycarbonyl)-L-serine tert-butyl ester
• CAS No.: 365455-30-7
• Molecular Formula: C₃₄H₄₈N₂O₁₀
• Molecular Weight: 644.763

Synonyms:O-(2-acetamido-3,4-di-O-benzyl-2-deoxy-α-D-galactopyranosyl)-N-(tert-butyloxycarbonyl)-L-serine tert-butyl ester

Chemical Property of O-(2-acetamido-3,4-di-O-benzyl-2-deoxy-α-D-galactopyranosyl)-N-(tert-butyloxycarbonyl)-L-serine tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of O-(2-acetamido-3,4-di-O-benzyl-2-deoxy-α-D-galactopyranosyl)-N-(tert-butyloxycarbonyl)-L-serine tert-butyl ester

There total 6 articles about O-(2-acetamido-3,4-di-O-benzyl-2-deoxy-α-D-galactopyranosyl)-N-(tert-butyloxycarbonyl)-L-serine tert-butyl 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: 26.0%

O-(3,4-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-2-deoxy-2-nitro-α-D-galactopyranosyl)-(1->3)-(4-O-acetyl-2-deoxy-2-nitro-6-O-(triisopropylsilyl)-α-D-galactopyranosyl)-N-(tert-butyloxycarbonyl)-L-serine tert-butyl ester (944065-05-8) + acetic anhydride (108-24-7) → O-(2-acetamido-3,4-di-O-benzyl-2-deoxy-6-O-(tert-butyldiphenylsilyl)-α-D-galactopyranosyl)-(1->3)-(4-O-acetyl-2-acetamido-2-deoxy-6-O-(triisopropylsilyl)-α-D-galactopyranosyl)-N-(tert-butyloxycarbonyl)-L-serine tert-butyl ester + O-(2-acetamido-3,4-di-O-benzyl-2-deoxy-α-D-galactopyranosyl)-N-(tert-butyloxycarbonyl)-L-serine tert-butyl ester (365455-30-7)

Guidance literature:

O-(3,4-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-2-deoxy-2-nitro-α-D-galactopyranosyl)-(1->3)-(4-O-acetyl-2-deoxy-2-nitro-6-O-(triisopropylsilyl)-α-D-galactopyranosyl)-N-(tert-butyloxycarbonyl)-L-serine tert-butyl ester; With hydrogen; platinized Raney nickel T₄; In ethanol; for 12h; under 2585.81 Torr;

acetic anhydride; With pyridine; Further stages.;

DOI:10.1021/jo061670b

Reference yield:

N-(tert-butyloxycarbonyl)-L-serine tert-butyl ester (71630-31-4,7738-22-9) → O-(2-acetamido-3,4-di-O-benzyl-2-deoxy-α-D-galactopyranosyl)-N-(tert-butyloxycarbonyl)-L-serine tert-butyl ester (365455-30-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 13 percent / potassium tert-butoxide / toluene; tetrahydrofuran / 1.5 h

2: 97 percent / tetrabutylammonium fluoride; acetic acid / tetrahydrofuran / 2 h / 20 °C

3: H₂ / platinized Raney nickel T₄ / ethanol / 12 h / 3878.71 Torr

4: 0.98 g / pyridine / 12 h

5: 0.92 g / sodium methoxide / methanol / 0.67 h

With pyridine; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; sodium methylate; acetic acid; platinized Raney nickel T₄; In tetrahydrofuran; methanol; ethanol; toluene;

DOI:10.1021/jo061670b

Reference yield:

O-(3,4-di-O-benzyl-2-deoxy-2-nitro-α-D-galactopyranosyl)-N-(tert-butyloxycarbonyl)-L-serine tert-butyl ester (365455-26-1) → O-(2-acetamido-3,4-di-O-benzyl-2-deoxy-α-D-galactopyranosyl)-N-(tert-butyloxycarbonyl)-L-serine tert-butyl ester (365455-30-7)

Guidance literature:

Multi-step reaction with 3 steps

1: H₂ / platinized Raney nickel T₄ / ethanol / 12 h / 3878.71 Torr

2: 0.98 g / pyridine / 12 h

3: 0.92 g / sodium methoxide / methanol / 0.67 h

With pyridine; hydrogen; sodium methylate; platinized Raney nickel T₄; In methanol; ethanol;

DOI:10.1021/jo061670b

upstream raw materials:

(S)-3-((2S,3R,4R,5R,6R)-6-Acetoxymethyl-3-acetylamino-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-2-tert-butoxycarbonylamino-propionic acid tert-butyl ester

O-(3,4-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-2-deoxy-2-nitro-α-D-galactopyranosyl)-(1->3)-(4-O-acetyl-2-deoxy-2-nitro-6-O-(triisopropylsilyl)-α-D-galactopyranosyl)-N-(tert-butyloxycarbonyl)-L-serine tert-butyl ester

acetic anhydride

N-(tert-butyloxycarbonyl)-L-serine tert-butyl ester

Downstream raw materials:

(S)-3-[(2S,3R,4R,5R,6R)-3-Acetylamino-6-((2S,3R,4R,5R,6R)-3-acetylamino-4,5-bis-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl)-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy]-2-tert-butoxycarbonylamino-propionic acid tert-butyl ester

3-{3-acetylamino-6-[3-acetylamino-4,5-bis-benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-pyran-2-yloxymethyl]-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy}-2-tert-butoxycarbonylamino-propionic acid tert-butyl ester

O-(3,4-di-O-benzyl-6-O-tert-butyldiphenylsilyl-2-deoxy-2-nitro-α-D-galactopyranosyl)-(1->6)-(2-acetamido-3,4-di-O-benzyl-2-deoxy-α-D-galactopyranosyl)-N-(tert-butyloxycarbonyl)-L-serine tert-butyl ester

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