(2R,3S,4S,6R)-4-Benzyloxy-6-(3-benzyloxy-propyl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-3-ol

Base Information

Chemical Name:(2R,3S,4S,6R)-4-Benzyloxy-6-(3-benzyloxy-propyl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-3-ol
CAS No.:736170-35-7
Molecular Formula:C₂₉H₄₄O₅Si
Molecular Weight:500.751
Hs Code.:

Synonyms:(2R,3S,4S,6R)-4-Benzyloxy-6-(3-benzyloxy-propyl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-3-ol

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Chemical Property of (2R,3S,4S,6R)-4-Benzyloxy-6-(3-benzyloxy-propyl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-3-ol

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Technology Process of (2R,3S,4S,6R)-4-Benzyloxy-6-(3-benzyloxy-propyl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-3-ol

There total 8 articles about (2R,3S,4S,6R)-4-Benzyloxy-6-(3-benzyloxy-propyl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-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: 99.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 189347-91-9
benzyl 3-(3-O-benzyl-2-deoxy-α-D-allopyranosyl)propyl ether

: 736170-35-7
(2R,3S,4S,6R)-4-Benzyloxy-6-(3-benzyloxy-propyl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-3-ol

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 23 ℃; for 2.66667h;
DOI:10.1016/j.tetlet.2004.05.020

Reference yield:

: 100-39-0
benzyl bromide

: 736170-35-7
(2R,3S,4S,6R)-4-Benzyloxy-6-(3-benzyloxy-propyl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-3-ol

Guidance literature:: Multi-step reaction with 3 steps

1: t-BuOK; Bu₄NI / tetrahydrofuran / 4 h / 23 °C

2: 94 percent / HCl / tetrahydrofuran; H₂O / 10 h / 23 °C

3: 99 percent / Et₃N; DMAP / CH₂Cl₂ / 2.67 h / 23 °C

With hydrogenchloride; dmap; potassium tert-butylate; tetra-(n-butyl)ammonium iodide; triethylamine; In tetrahydrofuran; dichloromethane; water;
DOI:10.1016/j.tetlet.2004.05.020

Reference yield:

: 187805-87-4
(2R,3S,4R,6R)-6-Allyl-2-hydroxymethyl-tetrahydro-pyran-3,4-diol

: 736170-35-7
(2R,3S,4S,6R)-4-Benzyloxy-6-(3-benzyloxy-propyl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-3-ol

Guidance literature:: Multi-step reaction with 7 steps

1.1: 79 percent / TsOH*H₂O / benzene; dimethylformamide / 7 h / Heating

2.1: (COCl)2; DMSO / CH₂Cl₂ / 0.25 h / -78 °C

2.2: 100 percent / Et₃N / CH₂Cl₂ / 0.5 h / -78 - 0 °C

3.1: 95 percent / K-Selectride / tetrahydrofuran / 1 h / -78 °C

4.1: 9-BBN / tetrahydrofuran / 1 h / 23 °C

4.2: TBHP; NaOH / tetrahydrofuran; H₂O / 0.67 h / 0 - 23 °C

5.1: t-BuOK; Bu₄NI / tetrahydrofuran / 4 h / 23 °C

6.1: 94 percent / HCl / tetrahydrofuran; H₂O / 10 h / 23 °C

7.1: 99 percent / Et₃N; DMAP / CH₂Cl₂ / 2.67 h / 23 °C

With hydrogenchloride; dmap; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; potassium tert-butylate; tetra-(n-butyl)ammonium iodide; potassium tri-sec-butyl-borohydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; benzene; 2.1: Swern oxidation / 2.2: Swern oxidation;
DOI:10.1016/j.tetlet.2004.05.020