(2S,3R,4R)-3-benzyloxy-1-tert-butyldiphenylsilyloxy-2,4-methylenedioxypentanal

Base Information

Chemical Name:(2S,3R,4R)-3-benzyloxy-1-tert-butyldiphenylsilyloxy-2,4-methylenedioxypentanal
CAS No.:289666-91-7
Molecular Formula:C₂₉H₃₄O₅Si
Molecular Weight:490.671
Hs Code.:

Synonyms:(2S,3R,4R)-3-benzyloxy-1-tert-butyldiphenylsilyloxy-2,4-methylenedioxypentanal

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2S,3R,4R)-3-benzyloxy-1-tert-butyldiphenylsilyloxy-2,4-methylenedioxypentanal

Chemical Property:

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Technology Process of (2S,3R,4R)-3-benzyloxy-1-tert-butyldiphenylsilyloxy-2,4-methylenedioxypentanal

There total 13 articles about (2S,3R,4R)-3-benzyloxy-1-tert-butyldiphenylsilyloxy-2,4-methylenedioxypentanal 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:

: 289666-90-6
(+)-(2R,3S,4R)-3-benzyloxy-1-tert-butyldiphenylsilyloxy-2,4-methylenedioxypentanol

: 289666-91-7
(2S,3R,4R)-3-benzyloxy-1-tert-butyldiphenylsilyloxy-2,4-methylenedioxypentanal

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - -30 ℃;
DOI:10.1021/ol052943c DOI:10.1021/jo060803q

Reference yield:

: (2RS,3R,4R)-3-benzyloxy-4,5-isopropylidenedioxy-1,2-pentanediol

: 289666-91-7
(2S,3R,4R)-3-benzyloxy-1-tert-butyldiphenylsilyloxy-2,4-methylenedioxypentanal

Guidance literature:: Multi-step reaction with 6 steps

1: 61 percent / DMAP; Et₃N / CH₂Cl₂ / 10 h / 20 °C

2: 98 percent / AcOH; H₂O / tetrahydrofuran / 6 h / 55 °C

3: 89 percent / pyridine / CH₂Cl₂ / 10 h / 20 °C

4: 88 percent / P₂O₅ / CH₂Cl₂ / 1.5 h

5: 99 percent / DIBALH / tetrahydrofuran / 1 h / 0 °C

6: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - -30 °C

With pyridine; dmap; oxalyl dichloride; water; phosphorus pentoxide; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; 6: Swern oxidation;
DOI:10.1021/jo060803q

Reference yield:

: 289666-86-0
(-)-(2R,3S,4R)-3-benzyloxy-5-tert-butyldiphenylsilyloxy-1,2,4-pentanetriol

: 289666-91-7
(2S,3R,4R)-3-benzyloxy-1-tert-butyldiphenylsilyloxy-2,4-methylenedioxypentanal

Guidance literature:: Multi-step reaction with 4 steps

1: 89 percent / pyridine / CH₂Cl₂ / 10 h / 20 °C

2: 88 percent / P₂O₅ / CH₂Cl₂ / 1.5 h

3: 99 percent / DIBALH / tetrahydrofuran / 1 h / 0 °C

4: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - -30 °C

With pyridine; oxalyl dichloride; phosphorus pentoxide; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; 4: Swern oxidation;
DOI:10.1021/jo060803q