(S)-3-Methyl-pentanoic acid (2R,3R,4S,5R,6R)-6-acetoxymethyl-2-((2S,3S,4R,5R)-3,4-bis-benzyloxy-2,5-bis-benzyloxymethyl-tetrahydro-furan-2-yloxy)-5-((S)-2-methyl-butyryloxy)-4-((S)-3-methyl-pentanoyloxy)-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: (S)-3-Methyl-pentanoic acid (2R,3R,4S,5R,6R)-6-acetoxymethyl-2-((2S,3S,4R,5R)-3,4-bis-benzyloxy-2,5-bis-benzyloxymethyl-tetrahydro-furan-2-yloxy)-5-((S)-2-methyl-butyryloxy)-4-((S)-3-methyl-pentanoyloxy)-tetrahydro-pyran-3-yl ester
• CAS No.: 178685-23-9
• Molecular Formula: C₅₉H₇₆O₁₅
• Molecular Weight: 1025.24

Synonyms:(S)-3-Methyl-pentanoic acid (2R,3R,4S,5R,6R)-6-acetoxymethyl-2-((2S,3S,4R,5R)-3,4-bis-benzyloxy-2,5-bis-benzyloxymethyl-tetrahydro-furan-2-yloxy)-5-((S)-2-methyl-butyryloxy)-4-((S)-3-methyl-pentanoyloxy)-tetrahydro-pyran-3-yl ester

Chemical Property of (S)-3-Methyl-pentanoic acid (2R,3R,4S,5R,6R)-6-acetoxymethyl-2-((2S,3S,4R,5R)-3,4-bis-benzyloxy-2,5-bis-benzyloxymethyl-tetrahydro-furan-2-yloxy)-5-((S)-2-methyl-butyryloxy)-4-((S)-3-methyl-pentanoyloxy)-tetrahydro-pyran-3-yl ester

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Technology Process of (S)-3-Methyl-pentanoic acid (2R,3R,4S,5R,6R)-6-acetoxymethyl-2-((2S,3S,4R,5R)-3,4-bis-benzyloxy-2,5-bis-benzyloxymethyl-tetrahydro-furan-2-yloxy)-5-((S)-2-methyl-butyryloxy)-4-((S)-3-methyl-pentanoyloxy)-tetrahydro-pyran-3-yl ester

There total 5 articles about (S)-3-Methyl-pentanoic acid (2R,3R,4S,5R,6R)-6-acetoxymethyl-2-((2S,3S,4R,5R)-3,4-bis-benzyloxy-2,5-bis-benzyloxymethyl-tetrahydro-furan-2-yloxy)-5-((S)-2-methyl-butyryloxy)-4-((S)-3-methyl-pentanoyloxy)-tetrahydro-pyran-3-yl 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: 93.0%

(3S)-methylvaleric acid (1730-92-3) + 6-O-acetyl-1',3',4',6'-tetra-O-benzyl-4-O-((S)-2-methylbutyryl)sucrose (178685-22-8) → (S)-3-Methyl-pentanoic acid (2R,3R,4S,5R,6R)-6-acetoxymethyl-2-((2S,3S,4R,5R)-3,4-bis-benzyloxy-2,5-bis-benzyloxymethyl-tetrahydro-furan-2-yloxy)-5-((S)-2-methyl-butyryloxy)-4-((S)-3-methyl-pentanoyloxy)-tetrahydro-pyran-3-yl ester (178685-23-9)

Guidance literature:

With 4-(Methylamino)pyridine; dicyclohexyl-carbodiimide; In tetrachloromethane; Ambient temperature;

DOI:10.1016/0008-6215(96)00026-2

Reference yield:

(S)-2-Methylbutyric acid (1730-91-2) → (S)-3-Methyl-pentanoic acid (2R,3R,4S,5R,6R)-6-acetoxymethyl-2-((2S,3S,4R,5R)-3,4-bis-benzyloxy-2,5-bis-benzyloxymethyl-tetrahydro-furan-2-yloxy)-5-((S)-2-methyl-butyryloxy)-4-((S)-3-methyl-pentanoyloxy)-tetrahydro-pyran-3-yl ester (178685-23-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 96 percent / dicyclohexylcarbodiimide, 4-methylaminopyridine / CCl₄ / Ambient temperature

2: 1.) tris(triphenylphosphine)rhodium(I) chloride, 2.) HgBr₂ / 1.) toluene, EtOH, H₂O, reflux, 24 h, 2.) toluene, EtOH, H₂O, 16 h

3: 74 percent / cerium(IV) ammonium nitrate / acetonitrile; H₂O / 1.5 h

4: 93 percent / dicyclohexylcarbodiimide, 4-methylaminopyridine / CCl₄ / Ambient temperature

With 4-(Methylamino)pyridine; Wilkinson's catalyst; ammonium cerium(IV) nitrate; dicyclohexyl-carbodiimide; mercury dibromide; In tetrachloromethane; water; acetonitrile;

DOI:10.1016/0008-6215(96)00026-2

Reference yield:

6-O-acetyl-3-O-allyl-1',3',4',6'-tetra-O-benzyl-2-O-(4-methoxybenzyl)sucrose (100980-32-3) → (S)-3-Methyl-pentanoic acid (2R,3R,4S,5R,6R)-6-acetoxymethyl-2-((2S,3S,4R,5R)-3,4-bis-benzyloxy-2,5-bis-benzyloxymethyl-tetrahydro-furan-2-yloxy)-5-((S)-2-methyl-butyryloxy)-4-((S)-3-methyl-pentanoyloxy)-tetrahydro-pyran-3-yl ester (178685-23-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 96 percent / dicyclohexylcarbodiimide, 4-methylaminopyridine / CCl₄ / Ambient temperature

2: 1.) tris(triphenylphosphine)rhodium(I) chloride, 2.) HgBr₂ / 1.) toluene, EtOH, H₂O, reflux, 24 h, 2.) toluene, EtOH, H₂O, 16 h

3: 74 percent / cerium(IV) ammonium nitrate / acetonitrile; H₂O / 1.5 h

4: 93 percent / dicyclohexylcarbodiimide, 4-methylaminopyridine / CCl₄ / Ambient temperature

With 4-(Methylamino)pyridine; Wilkinson's catalyst; ammonium cerium(IV) nitrate; dicyclohexyl-carbodiimide; mercury dibromide; In tetrachloromethane; water; acetonitrile;

DOI:10.1016/0008-6215(96)00026-2

upstream raw materials:

(3S)-methylvaleric acid

6-O-acetyl-1',3',4',6'-tetra-O-benzyl-4-O-((S)-2-methylbutyryl)sucrose

(S)-2-Methylbutyric acid

6-O-acetyl-3-O-allyl-1',3',4',6'-tetra-O-benzyl-2-O-(4-methoxybenzyl)sucrose

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