N⁶,N⁶-dibenzoyl-9-<3'-deoxy-3'-(p-toluenesulfonyl)-5'-O-(MMTr)-β-D-glyceropent-2-enofuranosyl>adenine

Base Information

• Chemical Name: N⁶,N⁶-dibenzoyl-9-<3'-deoxy-3'-(p-toluenesulfonyl)-5'-O-(MMTr)-β-D-glyceropent-2-enofuranosyl>adenine
• CAS No.: 119753-69-4
• Molecular Formula: C₅₁H₄₁N₅O₇S
• Molecular Weight: 867.982

Synonyms:N⁶,N⁶-dibenzoyl-9-<3'-deoxy-3'-(p-toluenesulfonyl)-5'-O-(MMTr)-β-D-glyceropent-2-enofuranosyl>adenine

Chemical Property of N⁶,N⁶-dibenzoyl-9-<3'-deoxy-3'-(p-toluenesulfonyl)-5'-O-(MMTr)-β-D-glyceropent-2-enofuranosyl>adenine

Chemical Property:

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Technology Process of N⁶,N⁶-dibenzoyl-9-<3'-deoxy-3'-(p-toluenesulfonyl)-5'-O-(MMTr)-β-D-glyceropent-2-enofuranosyl>adenine

There total 6 articles about N⁶,N⁶-dibenzoyl-9-<3'-deoxy-3'-(p-toluenesulfonyl)-5'-O-(MMTr)-β-D-glyceropent-2-enofuranosyl>adenine 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: 81.0%

N6,N6-dibenzoyl-9-<3'-deoxy-3'-(p-toluenesulfonyl)-5'-O-(MMTr)-β-D-xylofuranosyl>adenine (119753-68-3) → N6,N6-dibenzoyl-9-<3'-deoxy-3'-(p-toluenesulfonyl)-5'-O-(MMTr)-β-D-glyceropent-2-enofuranosyl>adenine (119753-69-4)

Guidance literature:

With pyridine; methanesulfonyl chloride; at 0 - 4 ℃; for 24h;

DOI:10.1016/S0040-4020(01)90111-5

Reference yield:

9-(2,3-anhydro-β-D-ribofuranosyl)adenine (2627-64-7) → N6,N6-dibenzoyl-9-<3'-deoxy-3'-(p-toluenesulfonyl)-5'-O-(MMTr)-β-D-glyceropent-2-enofuranosyl>adenine (119753-69-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) sodium methoxide / 1.) MeOH, 20 deg C, 2.) reflux

2: 1.) chlorotrimethylsilane, pyridine / 1.) 20 deg C, 2 h, 2.) 3 h

3: 93 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 1 h / 20 °C

4: 92 percent / pyridine / 24 h / 20 °C

5: 81 percent / methanesulfonyl chloride, pyridine / 24 h / 0 - 4 °C

With pyridine; chloro-trimethyl-silane; sodium methylate; methanesulfonyl chloride; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;

DOI:10.1016/S0040-4020(01)90111-5

Reference yield:

(2R,3S,4R,5R)-2-(6-Amino-purin-9-yl)-5-hydroxymethyl-4-p-tolylsulfanyl-tetrahydro-furan-3-ol → N6,N6-dibenzoyl-9-<3'-deoxy-3'-(p-toluenesulfonyl)-5'-O-(MMTr)-β-D-glyceropent-2-enofuranosyl>adenine (119753-69-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) chlorotrimethylsilane, pyridine / 1.) 20 deg C, 2 h, 2.) 3 h

2: 93 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 1 h / 20 °C

3: 92 percent / pyridine / 24 h / 20 °C

4: 81 percent / methanesulfonyl chloride, pyridine / 24 h / 0 - 4 °C

With pyridine; chloro-trimethyl-silane; methanesulfonyl chloride; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;

DOI:10.1016/S0040-4020(01)90111-5

upstream raw materials:

N⁶,N⁶-dibenzoyl-9-<3'-deoxy-3'-(p-toluenesulfonyl)-5'-O-(MMTr)-β-D-xylofuranosyl>adenine

9-(2,3-anhydro-β-D-ribofuranosyl)adenine

N⁶,N⁶-dibenzoyl-9-<3'-deoxy-3'-(p-toluenethio)-β-D-xylofuranosyl>adenine

N⁶,N⁶-dibenzoyl-9-<3'-deoxy-3'-(p-toluenesulfonyl)-β-D-xylofuranosyl>adenine

Downstream raw materials:

9-[(2R,3S,4R,5R)-5-[(4-Methoxy-phenyl)-diphenyl-methoxymethyl]-3-pyrrolidin-1-yl-4-(toluene-4-sulfonyl)-tetrahydro-furan-2-yl]-9H-purin-6-ylamine

9-[(2R,3S,4R,5R)-5-[(4-Methoxy-phenyl)-diphenyl-methoxymethyl]-3-piperidin-1-yl-4-(toluene-4-sulfonyl)-tetrahydro-furan-2-yl]-9H-purin-6-ylamine

(2R,3S,4R,5R)-2-(6-Amino-purin-9-yl)-5-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-4-(toluene-4-sulfonyl)-tetrahydro-furan-3-ol

9-[(2R,3S,4S,5R)-3-Amino-5-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-4-(toluene-4-sulfonyl)-tetrahydro-furan-2-yl]-9H-purin-6-ylamine

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