{(2R,3R,4S,5S,6R)-2-[(1R,2R)-3-Acetylamino-1-(acetylamino-methyl)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-propoxy]-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-4-yloxy}-acetic acid benzyl ester

Base Information

• Chemical Name: {(2R,3R,4S,5S,6R)-2-[(1R,2R)-3-Acetylamino-1-(acetylamino-methyl)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-propoxy]-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-4-yloxy}-acetic acid benzyl ester
• CAS No.: 181045-89-6
• Molecular Formula: C₇₁H₈₀N₂O₁₅
• Molecular Weight: 1201.42

Synonyms:

Chemical Property of {(2R,3R,4S,5S,6R)-2-[(1R,2R)-3-Acetylamino-1-(acetylamino-methyl)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-propoxy]-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-4-yloxy}-acetic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

Technology Process of {(2R,3R,4S,5S,6R)-2-[(1R,2R)-3-Acetylamino-1-(acetylamino-methyl)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-propoxy]-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-4-yloxy}-acetic acid benzyl ester

There total 5 articles about {(2R,3R,4S,5S,6R)-2-[(1R,2R)-3-Acetylamino-1-(acetylamino-methyl)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-propoxy]-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-4-yloxy}-acetic acid benzyl 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: 22.0%

(2,4,6-tri-O-benzyl-1-deoxy-1-methylsulfanyl-β-D-galactopyranos-3-yl)-acetic acid benzyl ester (165557-04-0) + N-[(2R,3R)-4-Acetylamino-3-hydroxy-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-butyl]-acetamide (181045-87-4) → {(2R,3R,4S,5S,6R)-2-[(1R,2R)-3-Acetylamino-1-(acetylamino-methyl)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-propoxy]-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-4-yloxy}-acetic acid benzyl ester (181045-89-6)

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; In acetonitrile; a) -30 deg C, 1 h, b) RT, overnight;

DOI:10.1016/0968-0896(96)00055-7

Reference yield:

(1-deoxy-1-methylsulfanyl-β-D-galactopyranos-3-yl)-acetic acid tert-butyl ester (165557-05-1) → {(2R,3R,4S,5S,6R)-2-[(1R,2R)-3-Acetylamino-1-(acetylamino-methyl)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-propoxy]-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-4-yloxy}-acetic acid benzyl ester (181045-89-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) NaH, 3.) AcOH

2: 1.) NaH / 1.) DMF, RT, 2 h, 2.) DMF, overnight

3: 22 percent / N-iodosuccinimide, triflic acid, molecular sieves 4A / acetonitrile / a) -30 deg C, 1 h, b) RT, overnight

With N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; sodium hydride; acetic acid; In acetonitrile;

DOI:10.1016/0968-0896(96)00055-7

Reference yield:

N-(4-acetylamino-2R,3R-dihydroxy-butyl)-acetamide (181045-85-2) → {(2R,3R,4S,5S,6R)-2-[(1R,2R)-3-Acetylamino-1-(acetylamino-methyl)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-propoxy]-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-4-yloxy}-acetic acid benzyl ester (181045-89-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) Br₂, 2.) Et₄NBr, molecular sieves 4A / 1.) CH₂Cl₂, 0 deg C, 5 min, 2.) DMF, 40 deg C, 2 h

2: 22 percent / N-iodosuccinimide, triflic acid, molecular sieves 4A / acetonitrile / a) -30 deg C, 1 h, b) RT, overnight

With N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; tetraethylammonium bromide; bromine; In acetonitrile;

DOI:10.1016/0968-0896(96)00055-7

upstream raw materials:

(2,4,6-tri-O-benzyl-1-deoxy-1-methylsulfanyl-β-D-galactopyranos-3-yl)-acetic acid benzyl ester

N-[(2R,3R)-4-Acetylamino-3-hydroxy-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-butyl]-acetamide

(1-deoxy-1-methylsulfanyl-β-D-galactopyranos-3-yl)-acetic acid tert-butyl ester

N-(4-acetylamino-2R,3R-dihydroxy-butyl)-acetamide

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