(+/-)-1,6-Di-O-benzyl-3,4-O-isopropylidene-2a,5-didehydro-2a-carba-α-psicofuranose

Base Information

• Chemical Name: (+/-)-1,6-Di-O-benzyl-3,4-O-isopropylidene-2a,5-didehydro-2a-carba-α-psicofuranose
• CAS No.: 132150-26-6
• Molecular Formula: C₂₄H₂₈O₅
• Molecular Weight: 396.483

Synonyms:(+/-)-1,6-Di-O-benzyl-3,4-O-isopropylidene-2a,5-didehydro-2a-carba-α-psicofuranose

Chemical Property of (+/-)-1,6-Di-O-benzyl-3,4-O-isopropylidene-2a,5-didehydro-2a-carba-α-psicofuranose

Chemical Property:

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Technology Process of (+/-)-1,6-Di-O-benzyl-3,4-O-isopropylidene-2a,5-didehydro-2a-carba-α-psicofuranose

There total 4 articles about (+/-)-1,6-Di-O-benzyl-3,4-O-isopropylidene-2a,5-didehydro-2a-carba-α-psicofuranose 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: 97.0%

(benzyloxymethyl)tributylstannane (66222-28-4) + (3aR*,6aR*)-6-Benzyloxymethyl-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-one (89291-75-8,117307-62-7) → (+/-)-1,6-Di-O-benzyl-3,4-O-isopropylidene-2a,5-didehydro-2a-carba-α-psicofuranose (132150-26-6)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; 1.) -65 deg C, 3 min, 2.) 10 min;

DOI:10.1021/jo00074a030

Reference yield: 68.0%

(+/-)-6-O-Benzyl-3,4-O-isopropylidene-1,2-anhydro-2a,5-didehydro-2a-carba-α-psicofuranose (132150-25-5) + benzyl alcohol (100-51-6,185532-71-2) → (+/-)-1,6-Di-O-benzyl-3,4-O-isopropylidene-2a,5-didehydro-2a-carba-α-psicofuranose (132150-26-6)

Guidance literature:

With sodium hydride; In tetrahydrofuran; 1.) r.t., 30 min, 2.) 32 h;

DOI:10.1021/jo00074a030

Reference yield: 68.0%

(+/-)-6-O-Benzyl-3,4-O-isopropylidene-1,2-anhydro-2a,5-didehydro-2a-carba-α-psicofuranose (132150-25-5) + sodium phenyl-methanolate (20194-18-7) → (+/-)-1,6-Di-O-benzyl-3,4-O-isopropylidene-2a,5-didehydro-2a-carba-α-psicofuranose (132150-26-6)

Guidance literature:

In tetrahydrofuran; for 32h; Ambient temperature;

DOI:10.1016/S0040-4039(00)98007-9

upstream raw materials:

(benzyloxymethyl)tributylstannane

(3aR*,6aR*)-6-Benzyloxymethyl-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-one

(+/-)-6-O-Benzyl-3,4-O-isopropylidene-1,2-anhydro-2a,5-didehydro-2a-carba-α-psicofuranose

sodium phenyl-methanolate

Downstream raw materials:

(1R,2S,5R)-5-Amino-3,5-bis-benzyloxymethyl-cyclopent-3-ene-1,2-diol

(+/-)-2-N-(5-Amino-6-chloropyrimidin-4-yl)-1,6-di-O-benzyl-2a,5-didehydro-2a-carba-β-psicofuranosylamine

(+/-)-9-<1,6-Di-O-benzyl-2a,5-didehydro-2a-carba-β-psicofuranosyl>adenine

(+/-)-9-<1,6-Di-O-benzyl-3,4-O-(ethoxymethylene)-2a,5-didehydro-2a-carba-β-psicofuranosyl>adenine

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