(2S)-[[2,7-dideoxy-6-C-methyl-3,4,6-tris-O-(phenylmethyl)-α-D-arabino-heptopyranosyl]oxy]propanoic acid ethyl ester

Base Information

• Chemical Name: (2S)-[[2,7-dideoxy-6-C-methyl-3,4,6-tris-O-(phenylmethyl)-α-D-arabino-heptopyranosyl]oxy]propanoic acid ethyl ester
• CAS No.: 249757-80-0
• Molecular Formula: C₃₄H₄₂O₇
• Molecular Weight: 562.703

Synonyms:(2S)-[[2,7-dideoxy-6-C-methyl-3,4,6-tris-O-(phenylmethyl)-α-D-arabino-heptopyranosyl]oxy]propanoic acid ethyl ester

Chemical Property of (2S)-[[2,7-dideoxy-6-C-methyl-3,4,6-tris-O-(phenylmethyl)-α-D-arabino-heptopyranosyl]oxy]propanoic acid ethyl ester

Chemical Property:

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Technology Process of (2S)-[[2,7-dideoxy-6-C-methyl-3,4,6-tris-O-(phenylmethyl)-α-D-arabino-heptopyranosyl]oxy]propanoic acid ethyl ester

There total 2 articles about (2S)-[[2,7-dideoxy-6-C-methyl-3,4,6-tris-O-(phenylmethyl)-α-D-arabino-heptopyranosyl]oxy]propanoic acid 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:

(S)-Ethyl lactate (687-47-8) + 1,5-anhydro-2,7-dideoxy-6-C-methyl-3,4,6-tris-O-(phenylmethyl)-D-arabino-hept-1-enitol (249757-75-3) → (2S)-[[2,7-dideoxy-6-C-methyl-3,4,6-tris-O-(phenylmethyl)-α-D-arabino-heptopyranosyl]oxy]propanoic acid ethyl ester (249757-80-0)

Guidance literature:

With triphenylphosphine hydrobromide; In dichloromethane; at 20 ℃;

DOI:10.1021/jo010880f

Reference yield:

(2S,3S,4R)-2-(1-Hydroxy-1-methyl-ethyl)-3,4-dihydro-2H-pyran-3,4-diol → (2S)-[[2,7-dideoxy-6-C-methyl-3,4,6-tris-O-(phenylmethyl)-α-D-arabino-heptopyranosyl]oxy]propanoic acid ethyl ester (249757-80-0)

Guidance literature:

Multi-step reaction with 2 steps

1: NaH; Bu₄NI / tetrahydrofuran / 20 °C

2: Ph₃P*HBr / CH₂Cl₂ / 20 °C

With triphenylphosphine hydrobromide; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo010880f

Reference yield:

(2S)-[[2,7-dideoxy-6-C-methyl-3,4,6-tris-O-(phenylmethyl)-α-D-arabino-heptopyranosyl]oxy]propanoic acid ethyl ester (249757-80-0) → (2S)-2-[[2,7-dideoxy-6-C-methyl-3,4,6-tris-O-(phenylmethyl)-α-D-arabino-heptopyranosyl]oxy]propanoic acid (249757-81-1)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; water; at 0 - 20 ℃;

DOI:10.1021/jo010880f

upstream raw materials:

(S)-Ethyl lactate

1,5-anhydro-2,7-dideoxy-6-C-methyl-3,4,6-tris-O-(phenylmethyl)-D-arabino-hept-1-enitol

Downstream raw materials:

(2S)-2-[[2,7-dideoxy-6-C-methyl-3,4,6-tris-O-(phenylmethyl)-α-D-arabino-heptopyranosyl]oxy]propanoic acid

(S)-2-[(2R,4R,5S,6S)-4,5-Bis-benzyloxy-6-(1-benzyloxy-1-methyl-ethyl)-tetrahydro-pyran-2-yloxy]-propionic acid 2-thioxo-2H-pyridin-1-yl ester

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