2,2-Dimethyl-propionic acid (2S,3S,4R)-5-benzyloxymethoxy-3-hydroxy-4-hydroxymethyl-2-methyl-pentyl ester

Base Information

Chemical Name:2,2-Dimethyl-propionic acid (2S,3S,4R)-5-benzyloxymethoxy-3-hydroxy-4-hydroxymethyl-2-methyl-pentyl ester
CAS No.:183017-32-5
Molecular Formula:C₂₀H₃₂O₆
Molecular Weight:368.47
Hs Code.:

Synonyms:2,2-Dimethyl-propionic acid (2S,3S,4R)-5-benzyloxymethoxy-3-hydroxy-4-hydroxymethyl-2-methyl-pentyl ester

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Chemical Property of 2,2-Dimethyl-propionic acid (2S,3S,4R)-5-benzyloxymethoxy-3-hydroxy-4-hydroxymethyl-2-methyl-pentyl ester

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Technology Process of 2,2-Dimethyl-propionic acid (2S,3S,4R)-5-benzyloxymethoxy-3-hydroxy-4-hydroxymethyl-2-methyl-pentyl ester

There total 5 articles about 2,2-Dimethyl-propionic acid (2S,3S,4R)-5-benzyloxymethoxy-3-hydroxy-4-hydroxymethyl-2-methyl-pentyl 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: 79.0%

: 183017-29-0
2,2-Dimethyl-propionic acid (2S,3S,4S)-4-benzyloxymethoxymethyl-3-hydroxy-5-(4-methoxy-benzyloxymethoxy)-2-methyl-pentyl ester

: 183017-32-5
2,2-Dimethyl-propionic acid (2S,3S,4R)-5-benzyloxymethoxy-3-hydroxy-4-hydroxymethyl-2-methyl-pentyl ester

Guidance literature:: With phosphate buffer pH 7; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; tert-butyl alcohol; for 4h; Ambient temperature;
DOI:10.1016/0040-4020(96)00751-X

Reference yield:

: 155781-15-0
(2R,3S)-2-[(S)-1-Benzyloxymethoxymethyl-2-(4-methoxy-benzyloxymethoxy)-ethyl]-3-methyl-oxirane

: 183017-32-5
2,2-Dimethyl-propionic acid (2S,3S,4R)-5-benzyloxymethoxy-3-hydroxy-4-hydroxymethyl-2-methyl-pentyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) CuCN, 2.) BF₃*Et₂O / 1.) Et₂O, from -78 deg C to -10 deg C, 2.) Et₂O a) -78 deg C, 2 h, b) -10 deg C, 20 h

2: 1.) O₃, Me₂S, 2.) NaBH₄ / 1.) MeOH, CH₂Cl₂, -78 deg C, 5 min, 2.) MeOH, CH₂Cl₂, -15 deg C, 30 min

3: 85 percent / pyridine / 5 h / 0 °C

4: 79 percent / DDQ, phosphate buffer pH 7 / CH₂Cl₂; 2-methyl-propan-2-ol / 4 h / Ambient temperature

With pyridine; sodium tetrahydroborate; dimethylsulfide; phosphate buffer pH 7; boron trifluoride diethyl etherate; ozone; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; tert-butyl alcohol;
DOI:10.1016/0040-4020(96)00751-X

Reference yield:

: 3282-30-2
pivaloyl chloride

: 183017-32-5
2,2-Dimethyl-propionic acid (2S,3S,4R)-5-benzyloxymethoxy-3-hydroxy-4-hydroxymethyl-2-methyl-pentyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 85 percent / pyridine / 5 h / 0 °C

2: 79 percent / DDQ, phosphate buffer pH 7 / CH₂Cl₂; 2-methyl-propan-2-ol / 4 h / Ambient temperature

With pyridine; phosphate buffer pH 7; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; tert-butyl alcohol;
DOI:10.1016/0040-4020(96)00751-X