(2R,3S,4R)-7-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-heptane-2,3,4-triol

Base Information

Chemical Name:(2R,3S,4R)-7-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-heptane-2,3,4-triol
CAS No.:188343-72-8
Molecular Formula:C₂₀H₃₆O₅Si
Molecular Weight:384.588
Hs Code.:

Synonyms:(2R,3S,4R)-7-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-heptane-2,3,4-triol

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Chemical Property of (2R,3S,4R)-7-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-heptane-2,3,4-triol

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Technology Process of (2R,3S,4R)-7-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-heptane-2,3,4-triol

There total 8 articles about (2R,3S,4R)-7-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-heptane-2,3,4-triol 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: 80.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 188343-64-8
(2R,3S,4R)-7-benzyloxy-1,2,3,4-tetrahydroxyheptane

: 188343-72-8
(2R,3S,4R)-7-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-heptane-2,3,4-triol

Guidance literature:: With pyridine; N,N,N',N'-tetramethylguanidine; In acetonitrile; for 3.5h; Ambient temperature;
DOI:10.1139/v97-010

Reference yield:

: 5470-84-8
4-benzyloxybutanal

: 188343-72-8
(2R,3S,4R)-7-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-heptane-2,3,4-triol

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) 1 N aq. NaOH, FDP aldolase, 2.) 1 N aq. HCl, acid phosphatase / 1.) DMF, RT, 67 h, 2.) DMF, RT, 24 h

2: 60 percent / NaBH(OAc)3, acetic acid / 3 h / 10 °C

3: 80 percent / TMG, pyridine / acetonitrile / 3.5 h / Ambient temperature

With pyridine; hydrogenchloride; sodium hydroxide; acid phosphatase; FDP aldolase; sodium tris(acetoxy)borohydride; acetic acid; N,N,N',N'-tetramethylguanidine; In acetonitrile;
DOI:10.1139/v97-010

Reference yield:

: 65371-70-2,77970-35-5,77970-36-6,88825-11-0
methyl 2,3-dideoxy-4,5:6,7-di-O-isopropylidene-D-arabino-hept-2-enonate

: 188343-72-8
(2R,3S,4R)-7-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-heptane-2,3,4-triol

Guidance literature:: Multi-step reaction with 5 steps

1: 96 percent / H₂ / Pd/C / ethanol / 18 h / 2068.6 Torr / Ambient temperature

2: 90 percent / LiAlH₄ / diethyl ether / a) 0 deg C, 0.5 h, 2.) RT, 14 h

3: 1.) NaH, 2.) Bu₄NI / 1.) THF, 0 deg C, 20 min, 2.) THF, a) 0 deg C, 30 min, b) RT, 24 h

4: 10 mg / Dowex 50W-X₈ resin / methanol; H₂O / 24 h

5: 80 percent / TMG, pyridine / acetonitrile / 3.5 h / Ambient temperature

With pyridine; lithium aluminium tetrahydride; Dowex 50W-X₈ resin; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; N,N,N',N'-tetramethylguanidine; palladium on activated charcoal; In methanol; diethyl ether; ethanol; water; acetonitrile;
DOI:10.1139/v97-010