(2R,3R,4S,5R,6R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-methoxy-6-((S)-1-methyl-pentyloxy)-tetrahydro-pyran

Base Information

• Chemical Name: (2R,3R,4S,5R,6R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-methoxy-6-((S)-1-methyl-pentyloxy)-tetrahydro-pyran
• CAS No.: 628316-28-9
• Molecular Formula: C₃₄H₄₄O₆
• Molecular Weight: 548.72

Synonyms:(2R,3R,4S,5R,6R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-methoxy-6-((S)-1-methyl-pentyloxy)-tetrahydro-pyran

Chemical Property of (2R,3R,4S,5R,6R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-methoxy-6-((S)-1-methyl-pentyloxy)-tetrahydro-pyran

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Technology Process of (2R,3R,4S,5R,6R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-methoxy-6-((S)-1-methyl-pentyloxy)-tetrahydro-pyran

There total 3 articles about (2R,3R,4S,5R,6R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-methoxy-6-((S)-1-methyl-pentyloxy)-tetrahydro-pyran 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:

(2R,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((S)-1-methyl-pentyloxy)-tetrahydro-pyran-3-ol (628315-91-3) + methyl iodide (74-88-4) → (2R,3R,4S,5R,6R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-methoxy-6-((S)-1-methyl-pentyloxy)-tetrahydro-pyran (628316-28-9)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 1h;

DOI:10.1021/ja036521e

Reference yield:

(S)-2-hexanol (52019-78-0) → (2R,3R,4S,5R,6R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-methoxy-6-((S)-1-methyl-pentyloxy)-tetrahydro-pyran (628316-28-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 36 percent / zinc chloride / diethyl ether; tetrahydrofuran / -78 - 20 °C

2: NaH / dimethylformamide / 1 h / 0 °C

With sodium hydride; zinc(II) chloride; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide;

DOI:10.1021/ja036521e

Reference yield:

3,4,6-tri-O-benzyl-D-glucal epoxide (74372-90-0) → (2R,3R,4S,5R,6R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-methoxy-6-((S)-1-methyl-pentyloxy)-tetrahydro-pyran (628316-28-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 36 percent / zinc chloride / diethyl ether; tetrahydrofuran / -78 - 20 °C

2: NaH / dimethylformamide / 1 h / 0 °C

With sodium hydride; zinc(II) chloride; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide;

DOI:10.1021/ja036521e

upstream raw materials:

(2R,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((S)-1-methyl-pentyloxy)-tetrahydro-pyran-3-ol

methyl iodide

(S)-2-hexanol

3,4,6-tri-O-benzyl-D-glucal epoxide

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