(S)-3-Methyl-pentanoic acid (2R,3R,4S,5R,6R)-6-acetoxymethyl-4-allyloxy-2-((2S,3S,4R,5R)-3,4-bis-benzyloxy-2,5-bis-benzyloxymethyl-tetrahydro-furan-2-yloxy)-5-((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-4-allyloxy-2-((2S,3S,4R,5R)-3,4-bis-benzyloxy-2,5-bis-benzyloxymethyl-tetrahydro-furan-2-yloxy)-5-((S)-3-methyl-pentanoyloxy)-tetrahydro-pyran-3-yl ester
CAS No.:178685-28-4
Molecular Formula:C₅₇H₇₂O₁₄
Molecular Weight:981.19
Hs Code.:

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

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

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

There total 2 articles about (S)-3-Methyl-pentanoic acid (2R,3R,4S,5R,6R)-6-acetoxymethyl-4-allyloxy-2-((2S,3S,4R,5R)-3,4-bis-benzyloxy-2,5-bis-benzyloxymethyl-tetrahydro-furan-2-yloxy)-5-((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: 67.0%

: 1730-92-3
(3S)-methylvaleric acid

: 178685-27-3
Acetic acid (2R,3R,4S,5R,6R)-4-allyloxy-6-((2S,3S,4R,5R)-3,4-bis-benzyloxy-2,5-bis-benzyloxymethyl-tetrahydro-furan-2-yloxy)-3,5-dihydroxy-tetrahydro-pyran-2-ylmethyl ester

: 178685-28-4
(S)-3-Methyl-pentanoic acid (2R,3R,4S,5R,6R)-6-acetoxymethyl-4-allyloxy-2-((2S,3S,4R,5R)-3,4-bis-benzyloxy-2,5-bis-benzyloxymethyl-tetrahydro-furan-2-yloxy)-5-((S)-3-methyl-pentanoyloxy)-tetrahydro-pyran-3-yl ester

Guidance literature:: With 4-(Methylamino)pyridine; dicyclohexyl-carbodiimide; In tetrachloromethane; Ambient temperature;
DOI:10.1016/0008-6215(96)00026-2

Reference yield:

: 100980-32-3
6-O-acetyl-3-O-allyl-1',3',4',6'-tetra-O-benzyl-2-O-(4-methoxybenzyl)sucrose

: 178685-28-4
(S)-3-Methyl-pentanoic acid (2R,3R,4S,5R,6R)-6-acetoxymethyl-4-allyloxy-2-((2S,3S,4R,5R)-3,4-bis-benzyloxy-2,5-bis-benzyloxymethyl-tetrahydro-furan-2-yloxy)-5-((S)-3-methyl-pentanoyloxy)-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 65 percent / cerium(IV) ammonium nitrate / acetonitrile; H₂O / 1.5 h

2: 67 percent / dicyclohexylcarbodiimide, 4-methylaminopyridine / CCl₄ / Ambient temperature

With 4-(Methylamino)pyridine; ammonium cerium(IV) nitrate; dicyclohexyl-carbodiimide; In tetrachloromethane; water; acetonitrile;
DOI:10.1016/0008-6215(96)00026-2

Reference yield:

: 178685-28-4
(S)-3-Methyl-pentanoic acid (2R,3R,4S,5R,6R)-6-acetoxymethyl-4-allyloxy-2-((2S,3S,4R,5R)-3,4-bis-benzyloxy-2,5-bis-benzyloxymethyl-tetrahydro-furan-2-yloxy)-5-((S)-3-methyl-pentanoyloxy)-tetrahydro-pyran-3-yl ester

: 178685-30-8
(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)-4-((S)-2-methyl-butyryloxy)-5-((S)-3-methyl-pentanoyloxy)-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 2 steps

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

2: 78 percent / dicyclohexylcarbodiimide, 4-methylaminopyridine / CCl₄ / Ambient temperature

With 4-(Methylamino)pyridine; Wilkinson's catalyst; dicyclohexyl-carbodiimide; mercury dibromide; In tetrachloromethane;
DOI:10.1016/0008-6215(96)00026-2