(3R,4R)-4-benzyloxy-5-(t-butyldimethylsiloxy)-2,2-dimethylpentane-1,3-diol

Base Information

Chemical Name:(3R,4R)-4-benzyloxy-5-(t-butyldimethylsiloxy)-2,2-dimethylpentane-1,3-diol
CAS No.:163275-46-5
Molecular Formula:C₂₀H₃₆O₄Si
Molecular Weight:368.589
Hs Code.:

Synonyms:(3R,4R)-4-benzyloxy-5-(t-butyldimethylsiloxy)-2,2-dimethylpentane-1,3-diol

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Chemical Property of (3R,4R)-4-benzyloxy-5-(t-butyldimethylsiloxy)-2,2-dimethylpentane-1,3-diol

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Technology Process of (3R,4R)-4-benzyloxy-5-(t-butyldimethylsiloxy)-2,2-dimethylpentane-1,3-diol

There total 10 articles about (3R,4R)-4-benzyloxy-5-(t-butyldimethylsiloxy)-2,2-dimethylpentane-1,3-diol 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: 85.0%

: 253662-88-3
(2R,4R)-2-(4-methoxyphenyl)-5,5-dimethyl-4-[(1S)-1-benzyloxy-2-(t-butyldimethylsiloxy)ethyl]-1,3-dioxane

: 201284-14-2
(3R,4S)-4-Benzyloxy-5-(tert-butyldimethylsiloxy)-3-(p-methoxybenzyloxy)-2,2-dimethylpentanol

: 163275-46-5
(3R,4R)-4-benzyloxy-5-(t-butyldimethylsiloxy)-2,2-dimethylpentane-1,3-diol

Guidance literature:: With dimethylsulfide borane complex; In toluene; for 0.5h; Heating;
DOI:10.1246/bcsj.74.113

Reference yield:

: 60856-63-5
(2R)-(-)-3,3-dimethylbutane-1,2,4-triol

: 163275-46-5
(3R,4R)-4-benzyloxy-5-(t-butyldimethylsiloxy)-2,2-dimethylpentane-1,3-diol

Guidance literature:: Multi-step reaction with 7 steps

1.1: camphorsulfonic acid / CH₂Cl₂ / 2 h / 20 °C

1.2: 92 percent / Et₃N / CH₂Cl₂

2.1: 21.2 g / oxalyl chloride; DMSO / CH₂Cl₂ / -78 - 20 °C

3.1: 86 percent / n-BuLi / hexane; tetrahydrofuran / -15 - 20 °C

4.1: OsO₄; N-methylmorpholine-N-oxide / H₂O; acetone; 2-methyl-propan-2-ol / 72 h / 2 °C

5.1: 100 percent / imidazole / dimethylformamide / 1 h / 0 °C

6.1: 96 percent / NaH / tetrahydrofuran; dimethylformamide / 18 h / 0 - 20 °C

7.1: 11 percent / BH₃*Me₂S / toluene / 0.5 h / Heating

With 1H-imidazole; osmium(VIII) oxide; n-butyllithium; oxalyl dichloride; dimethylsulfide borane complex; camphor-10-sulfonic acid; sodium hydride; dimethyl sulfoxide; 4-methylmorpholine N-oxide; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol; 2.1: Swern's oxidation / 3.1: Wittig reaction;
DOI:10.1246/bcsj.74.113

Reference yield:

: 599-04-2
(R)-Pantolacton

: 163275-46-5
(3R,4R)-4-benzyloxy-5-(t-butyldimethylsiloxy)-2,2-dimethylpentane-1,3-diol

Guidance literature:: Multi-step reaction with 8 steps

1.1: 51.0 g / LiAlH₄ / tetrahydrofuran / 4 h / 0 - 20 °C

2.1: camphorsulfonic acid / CH₂Cl₂ / 2 h / 20 °C

2.2: 92 percent / Et₃N / CH₂Cl₂

3.1: 21.2 g / oxalyl chloride; DMSO / CH₂Cl₂ / -78 - 20 °C

4.1: 86 percent / n-BuLi / hexane; tetrahydrofuran / -15 - 20 °C

5.1: OsO₄; N-methylmorpholine-N-oxide / H₂O; acetone; 2-methyl-propan-2-ol / 72 h / 2 °C

6.1: 100 percent / imidazole / dimethylformamide / 1 h / 0 °C

7.1: 96 percent / NaH / tetrahydrofuran; dimethylformamide / 18 h / 0 - 20 °C

8.1: 11 percent / BH₃*Me₂S / toluene / 0.5 h / Heating

With 1H-imidazole; osmium(VIII) oxide; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; dimethylsulfide borane complex; camphor-10-sulfonic acid; sodium hydride; dimethyl sulfoxide; 4-methylmorpholine N-oxide; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol; 3.1: Swern's oxidation / 4.1: Wittig reaction;
DOI:10.1246/bcsj.74.113