Acetic acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-(2-thioxo-2λ⁵-[1,3,2]oxathiaphospholan-2-yloxymethyl)-tetrahydro-furan-3-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-(2-thioxo-2λ⁵-[1,3,2]oxathiaphospholan-2-yloxymethyl)-tetrahydro-furan-3-yl ester
• CAS No.: 462104-08-1
• Molecular Formula: C₂₁H₂₂N₅O₆PS₂
• Molecular Weight: 535.541

Synonyms:Acetic acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-(2-thioxo-2λ⁵-[1,3,2]oxathiaphospholan-2-yloxymethyl)-tetrahydro-furan-3-yl ester

Chemical Property of Acetic acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-(2-thioxo-2λ⁵-[1,3,2]oxathiaphospholan-2-yloxymethyl)-tetrahydro-furan-3-yl ester

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Technology Process of Acetic acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-(2-thioxo-2λ⁵-[1,3,2]oxathiaphospholan-2-yloxymethyl)-tetrahydro-furan-3-yl ester

There total 1 articles about Acetic acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-(2-thioxo-2λ⁵-[1,3,2]oxathiaphospholan-2-yloxymethyl)-tetrahydro-furan-3-yl ester 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: 84.0%

3'-O-acetyl-N-benzoyl-2'-deoxyadenosine (25152-95-8) + 2-chloro-1,3,2-oxathiaphospholane (20354-32-9) → Acetic acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-(2-thioxo-2λ5-[1,3,2]oxathiaphospholan-2-yloxymethyl)-tetrahydro-furan-3-yl ester (462104-08-1)

Guidance literature:

With pyridine; sulfur; for 16h;

DOI:10.1021/ol050617r

Reference yield:

Acetic acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-(2-thioxo-2λ5-[1,3,2]oxathiaphospholan-2-yloxymethyl)-tetrahydro-furan-3-yl ester (462104-08-1) → C19H18N5O13P3S(4-)

Guidance literature:

With tris(tetra-n-butylammonium) hydrogen pyrophosphate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; for 2h;

DOI:10.1021/ol050617r

Reference yield:

Acetic acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-(2-thioxo-2λ5-[1,3,2]oxathiaphospholan-2-yloxymethyl)-tetrahydro-furan-3-yl ester (462104-08-1) → dATP(α-S) (64145-28-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent Spectr_. / DBU; tris(tetra-n-butylammonium) pyrophosphate / acetonitrile / 2 h

2: ammonia / acetonitrile / 6 h / 55 °C

With ammonia; tris(tetra-n-butylammonium) hydrogen pyrophosphate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile;

DOI:10.1021/ol050617r

upstream raw materials:

3'-O-acetyl-N-benzoyl-2'-deoxyadenosine

2-chloro-1,3,2-oxathiaphospholane

Downstream raw materials:

dATP(α-S)

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