(2S,3S,4S,5R)-4,5-Bis-benzyloxy-2-methoxy-2-oxo-2λ⁵-[1,2]oxaphosphinan-3-ol

Base Information

• Chemical Name: (2S,3S,4S,5R)-4,5-Bis-benzyloxy-2-methoxy-2-oxo-2λ⁵-[1,2]oxaphosphinan-3-ol
• CAS No.: 195004-90-1
• Molecular Formula: C₁₉H₂₃O₆P
• Molecular Weight: 378.362

Synonyms:(2S,3S,4S,5R)-4,5-Bis-benzyloxy-2-methoxy-2-oxo-2λ⁵-[1,2]oxaphosphinan-3-ol

Chemical Property of (2S,3S,4S,5R)-4,5-Bis-benzyloxy-2-methoxy-2-oxo-2λ⁵-[1,2]oxaphosphinan-3-ol

Chemical Property:

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Technology Process of (2S,3S,4S,5R)-4,5-Bis-benzyloxy-2-methoxy-2-oxo-2λ⁵-[1,2]oxaphosphinan-3-ol

There total 1 articles about (2S,3S,4S,5R)-4,5-Bis-benzyloxy-2-methoxy-2-oxo-2λ⁵-[1,2]oxaphosphinan-3-ol 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: 19.0%

((2S,3R)-2,3-Bis-benzyloxy-4-formyloxy-1-hydroxy-butyl)-phosphonic acid dimethyl ester → (2S,3S,4S,5R)-4,5-Bis-benzyloxy-2-methoxy-2-oxo-2λ5-[1,2]oxaphosphinan-3-ol (195004-90-1) + (2S,3R,4S,5R)-4,5-Bis-benzyloxy-2-methoxy-2-oxo-2λ5-[1,2]oxaphosphinan-3-ol + (2R,3S,4S,5R)-4,5-Bis-benzyloxy-2-methoxy-2-oxo-2λ5-[1,2]oxaphosphinan-3-ol (195004-92-3) + (2R,3R,4S,5R)-4,5-Bis-benzyloxy-2-methoxy-2-oxo-2λ5-[1,2]oxaphosphinan-3-ol

Guidance literature:

With sodium methylate; In methanol; for 4h; Yields of byproduct given; Ambient temperature;

DOI:10.1021/jo9706382

Reference yield: 71.0%

benzyl bromide (100-39-0) + (2S,3S,4S,5R)-4,5-Bis-benzyloxy-2-methoxy-2-oxo-2λ5-[1,2]oxaphosphinan-3-ol (195004-90-1) → (2S,3S,4S,5R)-3,4,5-Tris-benzyloxy-2-methoxy-[1,2]oxaphosphinane 2-oxide (195004-98-9)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; paraffin; at 25 ℃; for 2.5h;

DOI:10.1021/jo9706382

Reference yield:

(2S,3S,4S,5R)-4,5-Bis-benzyloxy-2-methoxy-2-oxo-2λ5-[1,2]oxaphosphinan-3-ol (195004-90-1) → (2S,3S,4S,5R)-3,4,5-Tris-benzyloxy-2-oxo-2λ5-[1,2]oxaphosphinan-2-ol

Guidance literature:

Multi-step reaction with 2 steps

1: 71 percent / NaH, n-Bu₄NI / paraffin; tetrahydrofuran / 2.5 h / 25 °C

2: 1.) Me₃SiBr, 2.) 3 N HCl / 1.) CH₂Cl₂, reflux, 1 h, 2.) 25 deg C, 15 min

With hydrogenchloride; trimethylsilyl bromide; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; paraffin;

DOI:10.1021/jo9706382

Downstream raw materials:

(2S,3S,4S,5R)-3,4,5-Tris-benzyloxy-2-methoxy-[1,2]oxaphosphinane 2-oxide

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