(R)-2-[(2R,3S,4R,5R,6S)-2-Acetoxymethyl-5-acetylamino-3-((2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-6-hydroxy-tetrahydro-pyran-4-yloxy]-propionic acid 2-benzenesulfonyl-ethyl ester

Base Information

• Chemical Name: (R)-2-[(2R,3S,4R,5R,6S)-2-Acetoxymethyl-5-acetylamino-3-((2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-6-hydroxy-tetrahydro-pyran-4-yloxy]-propionic acid 2-benzenesulfonyl-ethyl ester
• CAS No.: 917030-07-0
• Molecular Formula: C₃₅H₄₈N₂O₁₉S
• Molecular Weight: 832.834
• Mol file: 917030-07-0.mol

Synonyms:(R)-2-[(2R,3S,4R,5R,6S)-2-Acetoxymethyl-5-acetylamino-3-((2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-6-hydroxy-tetrahydro-pyran-4-yloxy]-propionic acid 2-benzenesulfonyl-ethyl ester

Chemical Property of (R)-2-[(2R,3S,4R,5R,6S)-2-Acetoxymethyl-5-acetylamino-3-((2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-6-hydroxy-tetrahydro-pyran-4-yloxy]-propionic acid 2-benzenesulfonyl-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-[(2R,3S,4R,5R,6S)-2-Acetoxymethyl-5-acetylamino-3-((2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-6-hydroxy-tetrahydro-pyran-4-yloxy]-propionic acid 2-benzenesulfonyl-ethyl ester

There total 14 articles about (R)-2-[(2R,3S,4R,5R,6S)-2-Acetoxymethyl-5-acetylamino-3-((2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-6-hydroxy-tetrahydro-pyran-4-yloxy]-propionic acid 2-benzenesulfonyl-ethyl 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: 95.0%

benzyl 3,4,6-tri-O-acethyl-2-deoxy-2-acetamido-β-D-glucopyranosyl-(1->4)-2-acetamido-6-O-acetyl-2-deoxy-3-O-(D-1-{[2-(phenylsulfonyl)ethoxy]carbonyl}ethyl)-α-D-glucopyranoside (917029-93-7) → (R)-2-[(2R,3S,4R,5R,6S)-2-Acetoxymethyl-5-acetylamino-3-((2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-6-hydroxy-tetrahydro-pyran-4-yloxy]-propionic acid 2-benzenesulfonyl-ethyl ester (917030-07-0)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; under 760.051 Torr;

DOI:10.1021/ja302099u

Reference yield:

2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranose (172490-46-9) → (R)-2-[(2R,3S,4R,5R,6S)-2-Acetoxymethyl-5-acetylamino-3-((2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-6-hydroxy-tetrahydro-pyran-4-yloxy]-propionic acid 2-benzenesulfonyl-ethyl ester (917030-07-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 98 percent / pyridine / 12 h / 20 °C

2: 96 percent / HBr; AcOH / CH₂Cl₂ / 4 h / 0 - 20 °C

3: 55 percent / 4 Angstroem molecular sieves; AgOTf / CH₂Cl₂

4: ZnCl₂; AcOH

5: 2.1 g / AcOH; Zn / tetrahydrofuran

6: 92 percent / H₂ / Pd/C / tetrahydrofuran; methanol / 2 h / 20 °C

With pyridine; 4 A molecular sieve; hydrogen bromide; hydrogen; silver trifluoromethanesulfonate; acetic acid; zinc(II) chloride; zinc; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1135/cccc20051615

Reference yield:

1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranose (122210-01-9,122210-05-3,145416-95-1,146864-65-5,114360-77-9) → (R)-2-[(2R,3S,4R,5R,6S)-2-Acetoxymethyl-5-acetylamino-3-((2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-6-hydroxy-tetrahydro-pyran-4-yloxy]-propionic acid 2-benzenesulfonyl-ethyl ester (917030-07-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 96 percent / HBr; AcOH / CH₂Cl₂ / 4 h / 0 - 20 °C

2: 55 percent / 4 Angstroem molecular sieves; AgOTf / CH₂Cl₂

3: ZnCl₂; AcOH

4: 2.1 g / AcOH; Zn / tetrahydrofuran

5: 92 percent / H₂ / Pd/C / tetrahydrofuran; methanol / 2 h / 20 °C

With 4 A molecular sieve; hydrogen bromide; hydrogen; silver trifluoromethanesulfonate; acetic acid; zinc(II) chloride; zinc; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1135/cccc20051615

upstream raw materials:

benzyl 3,4,6-tri-O-acethyl-2-deoxy-2-acetamido-β-D-glucopyranosyl-(1->4)-2-acetamido-6-O-acetyl-2-deoxy-3-O-(D-1-{[2-(phenylsulfonyl)ethoxy]carbonyl}ethyl)-α-D-glucopyranoside

benzyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-(D-1-{[2-(phenylsulfonyl)ethoxy]carbonyl}ethyl)-α-D-glucopyranoside

benzyl 3,4,6-tri-O-acetyl-2-deoxy-2-[(2,2,2-trichloroethoxy)carbonylamino]-β-D-glucopyranosyl-(1->4)-2-acetamido-6-O-benzyl-2-deoxy-3-O-(D-1-{[2-(phenylsulfonyl)ethoxy]carbonyl}ethyl)-α-D-glucopyranoside

benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside

Downstream raw materials:

(R)-2-[(2R,3S,4R,5R,6R)-2-Acetoxymethyl-5-acetylamino-3-((2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-6-phosphonooxy-tetrahydro-pyran-4-yloxy]-propionic acid 2-benzenesulfonyl-ethyl ester

dibenzyl 3,4,6-tri-O-acetyl-2-deoxy-2-acetamido-β-D-glucopyranosyl-(1->4)-2-acetamido-6-O-acetyl-2-deoxy-3-O-(D-1-{[N-hydroxysuccinimidyloxy)carbonyl]ethyl}-α-D-glucopyranosyl phosphate

dibenzyl 3,4,6-tri-O-acethyl-2-deoxy-2-acetamido-β-D-glucopyranosyl-(1->4)-2-acetamido-6-O-acetyl-2-deoxy-3-O-(D-1-{[2-(phenylsulfonyl)ethoxy]carbonyl}ethyl)-α-D-glucopyranosyl phosphate

dibenzyl 3,4,6-tri-O-acetyl-2-deoxy-2-acetamido-β-D-glucopyranosyl-(1->4)-2-acetamido-6-O-acetyl-2-deoxy-3-O-(D-2-propionyl-L-alanyl-D-glutamic diamide)-α-D-glucopyranosyl phosphate