9-[3-C-(benzyloxymethyl)-2,3-dideoxy-3-C-methyl-β-D-glycero-tetrofuranosyl]6-chloropurine and 9-[3-C-(benzyloxymethyl)-2,3-dideoxy-3-C-methyl-α-D-glycero-tetrofuranosyl]6-chloropurine

Base Information

Chemical Name:9-[3-C-(benzyloxymethyl)-2,3-dideoxy-3-C-methyl-β-D-glycero-tetrofuranosyl]6-chloropurine and 9-[3-C-(benzyloxymethyl)-2,3-dideoxy-3-C-methyl-α-D-glycero-tetrofuranosyl]6-chloropurine
CAS No.:301826-28-8
Molecular Formula:C₁₈H₁₉ClN₄O₂
Molecular Weight:358.827
Hs Code.:

9-[3-C-(benzyloxymethyl)-2,3-dideoxy-3-C-methyl-β-D-glycero-tetrofuranosyl]6-chloropurine and 9-[3-C-(benzyloxymethyl)-2,3-dideoxy-3-C-methyl-α-D-glycero-tetrofuranosyl]6-chloropurine

Synonyms:9-[3-C-(benzyloxymethyl)-2,3-dideoxy-3-C-methyl-β-D-glycero-tetrofuranosyl]6-chloropurine and 9-[3-C-(benzyloxymethyl)-2,3-dideoxy-3-C-methyl-α-D-glycero-tetrofuranosyl]6-chloropurine

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Chemical Property of 9-[3-C-(benzyloxymethyl)-2,3-dideoxy-3-C-methyl-β-D-glycero-tetrofuranosyl]6-chloropurine and 9-[3-C-(benzyloxymethyl)-2,3-dideoxy-3-C-methyl-α-D-glycero-tetrofuranosyl]6-chloropurine

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Technology Process of 9-[3-C-(benzyloxymethyl)-2,3-dideoxy-3-C-methyl-β-D-glycero-tetrofuranosyl]6-chloropurine and 9-[3-C-(benzyloxymethyl)-2,3-dideoxy-3-C-methyl-α-D-glycero-tetrofuranosyl]6-chloropurine

There total 3 articles about 9-[3-C-(benzyloxymethyl)-2,3-dideoxy-3-C-methyl-β-D-glycero-tetrofuranosyl]6-chloropurine and 9-[3-C-(benzyloxymethyl)-2,3-dideoxy-3-C-methyl-α-D-glycero-tetrofuranosyl]6-chloropurine 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: 62.0%

: 32865-86-4
6-chloro-9-trimethylsilylpurine

: 301826-40-4
1-O-acetyl-3-C-(benzyloxymethyl)-2,3-dideoxy-3-C-methyl-D-glycero-tetrofuranose

: 301826-28-8
9-[3-C-(benzyloxymethyl)-2,3-dideoxy-3-C-methyl-β-D-glycero-tetrofuranosyl]6-chloropurine and 9-[3-C-(benzyloxymethyl)-2,3-dideoxy-3-C-methyl-α-D-glycero-tetrofuranosyl]6-chloropurine

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; 1,2-dichloro-ethane; at 20 ℃; for 2h;
DOI:10.1016/S0008-6215(00)00005-7

Reference yield:

: 220569-97-1
3-C-(benzyloxymethyl)-2,3-dideoxy-3-C-methyl-D-glycero-tetrofuranose

: 301826-28-8
9-[3-C-(benzyloxymethyl)-2,3-dideoxy-3-C-methyl-β-D-glycero-tetrofuranosyl]6-chloropurine and 9-[3-C-(benzyloxymethyl)-2,3-dideoxy-3-C-methyl-α-D-glycero-tetrofuranosyl]6-chloropurine

Guidance literature:: Multi-step reaction with 2 steps

1: 89.2 percent / pyridine

2: 62 percent / (CH₃)3SiOTf / CH₂Cl₂; 1,2-dichloro-ethane / 2 h / 20 °C

With trimethylsilyl trifluoromethanesulfonate; pyridine; In dichloromethane; 1,2-dichloro-ethane; 1: Acetylation / 2: Alkylation;
DOI:10.1016/S0008-6215(00)00005-7

Reference yield:

: 220569-96-0
ethyl (R)-3-benzyloxymethyl-3-methyl-4-oxobutyrate

: 301826-28-8
9-[3-C-(benzyloxymethyl)-2,3-dideoxy-3-C-methyl-β-D-glycero-tetrofuranosyl]6-chloropurine and 9-[3-C-(benzyloxymethyl)-2,3-dideoxy-3-C-methyl-α-D-glycero-tetrofuranosyl]6-chloropurine

Guidance literature:: Multi-step reaction with 3 steps

1: 67.2 percent / DIBAL-H / toluene / 3 h / -78 °C

2: 89.2 percent / pyridine

3: 62 percent / (CH₃)3SiOTf / CH₂Cl₂; 1,2-dichloro-ethane / 2 h / 20 °C

With trimethylsilyl trifluoromethanesulfonate; diisobutylaluminium hydride; pyridine; In dichloromethane; 1,2-dichloro-ethane; toluene; 1: Reduction / 2: Acetylation / 3: Alkylation;
DOI:10.1016/S0008-6215(00)00005-7