(2R,3R,4S,5R,6S)-5-(benzyloxy)-2-((benzyloxy)methyl)-4-hydroxy-6-(((2R,3R,4S,5R,6R)-4,5,6-tris(benzyloxy)-2-((benzyloxy)methyl)tetrahydro-2H-pyran-3-yl)oxy)tetrahydro-2H-pyran-3-yl acetate

Base Information

• Chemical Name: (2R,3R,4S,5R,6S)-5-(benzyloxy)-2-((benzyloxy)methyl)-4-hydroxy-6-(((2R,3R,4S,5R,6R)-4,5,6-tris(benzyloxy)-2-((benzyloxy)methyl)tetrahydro-2H-pyran-3-yl)oxy)tetrahydro-2H-pyran-3-yl acetate
• CAS No.: 121237-39-6
• Molecular Formula: C₅₆H₆₀O₁₂
• Molecular Weight: 925.085

Synonyms:(2R,3R,4S,5R,6S)-5-(benzyloxy)-2-((benzyloxy)methyl)-4-hydroxy-6-(((2R,3R,4S,5R,6R)-4,5,6-tris(benzyloxy)-2-((benzyloxy)methyl)tetrahydro-2H-pyran-3-yl)oxy)tetrahydro-2H-pyran-3-yl acetate

Chemical Property of (2R,3R,4S,5R,6S)-5-(benzyloxy)-2-((benzyloxy)methyl)-4-hydroxy-6-(((2R,3R,4S,5R,6R)-4,5,6-tris(benzyloxy)-2-((benzyloxy)methyl)tetrahydro-2H-pyran-3-yl)oxy)tetrahydro-2H-pyran-3-yl acetate

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Technology Process of (2R,3R,4S,5R,6S)-5-(benzyloxy)-2-((benzyloxy)methyl)-4-hydroxy-6-(((2R,3R,4S,5R,6R)-4,5,6-tris(benzyloxy)-2-((benzyloxy)methyl)tetrahydro-2H-pyran-3-yl)oxy)tetrahydro-2H-pyran-3-yl acetate

There total 10 articles about (2R,3R,4S,5R,6S)-5-(benzyloxy)-2-((benzyloxy)methyl)-4-hydroxy-6-(((2R,3R,4S,5R,6R)-4,5,6-tris(benzyloxy)-2-((benzyloxy)methyl)tetrahydro-2H-pyran-3-yl)oxy)tetrahydro-2H-pyran-3-yl acetate 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: 97.0%

Trimethyl orthoacetate (1445-45-0) + benzyl 2,3,6-tri-O-benzyl-4-O-(2,6-di-O-benzyl-β-D-galactopyranosyl)-β-D-glucopyranoside (94926-36-0) → (2R,3R,4S,5R,6S)-5-(benzyloxy)-2-((benzyloxy)methyl)-4-hydroxy-6-(((2R,3R,4S,5R,6R)-4,5,6-tris(benzyloxy)-2-((benzyloxy)methyl)tetrahydro-2H-pyran-3-yl)oxy)tetrahydro-2H-pyran-3-yl acetate (121237-39-6)

Guidance literature:

With toluene-4-sulfonic acid; In acetonitrile; for 0.166667h; Ambient temperature;

Reference yield: 69.0%

benzyl (2,6-di-O-benzyl-3,4-O-(ethyl orthoacetyl)-β-D-galactopyranosyl)-(1→4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside → (2R,3R,4S,5R,6S)-5-(benzyloxy)-2-((benzyloxy)methyl)-4-hydroxy-6-(((2R,3R,4S,5R,6R)-4,5,6-tris(benzyloxy)-2-((benzyloxy)methyl)tetrahydro-2H-pyran-3-yl)oxy)tetrahydro-2H-pyran-3-yl acetate (121237-39-6)

Guidance literature:

With acetic acid; In water; at 20 ℃; for 0.25h;

DOI:10.2174/1570178612666150415235934

Reference yield: 54.0%

benzyl 2'',6''-di-O-benzyl-β-galactopyranosyl-(1''->4')-2',3',6'-tri-O-benzyl-α,β-glucopyranoside + Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-diacetylamino-6-methylsulfanyl-tetrahydro-pyran-4-yl ester (171973-78-7) → (2R,3R,4S,5R,6S)-5-(benzyloxy)-2-((benzyloxy)methyl)-4-hydroxy-6-(((2R,3R,4S,5R,6R)-4,5,6-tris(benzyloxy)-2-((benzyloxy)methyl)tetrahydro-2H-pyran-3-yl)oxy)tetrahydro-2H-pyran-3-yl acetate (121237-39-6) + C70H79NO20

Guidance literature:

With dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; In dichloromethane; at 5 ℃;

DOI:10.1016/00404-0399(50)14068-

upstream raw materials:

Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-diacetylamino-6-methylsulfanyl-tetrahydro-pyran-4-yl ester

Trimethyl orthoacetate

benzyl 2,3,6-tri-O-benzyl-4-O-(2,6-di-O-benzyl-β-D-galactopyranosyl)-β-D-glucopyranoside

1',2',3',6',2,3,4,6-octa-O-acetyl-β-D-lactose

Downstream raw materials:

Benzyl-O-(3,4,6-tri-O-acetyl-2-desoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-O-(4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranosid

benzyl O-[3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl]-(1->3)-O-(2,6-di-O-benzyl-4-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

Benzyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-(1->3)-O-(4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranosid

Benzyl-O-(2-acetamido-2-desoxy-β-D-glucopyranosyl)-(1->3)-O-(2,6-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranosid

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