(1S,3S,4S,5R)-1,6:7,8-bis-O-isopropylidene-3-(4'-nitrobenzoyl)-1,4,5-tris(hydroxymethyl)cyclopentane-1,3-diol

Base Information

• Chemical Name: (1S,3S,4S,5R)-1,6:7,8-bis-O-isopropylidene-3-(4'-nitrobenzoyl)-1,4,5-tris(hydroxymethyl)cyclopentane-1,3-diol
• CAS No.: 442906-69-6
• Molecular Formula: C₂₁H₂₇NO₈
• Molecular Weight: 421.447
• Mol file: 442906-69-6.mol

Synonyms:(1S,3S,4S,5R)-1,6:7,8-bis-O-isopropylidene-3-(4'-nitrobenzoyl)-1,4,5-tris(hydroxymethyl)cyclopentane-1,3-diol

Chemical Property of (1S,3S,4S,5R)-1,6:7,8-bis-O-isopropylidene-3-(4'-nitrobenzoyl)-1,4,5-tris(hydroxymethyl)cyclopentane-1,3-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,3S,4S,5R)-1,6:7,8-bis-O-isopropylidene-3-(4'-nitrobenzoyl)-1,4,5-tris(hydroxymethyl)cyclopentane-1,3-diol

There total 2 articles about (1S,3S,4S,5R)-1,6:7,8-bis-O-isopropylidene-3-(4'-nitrobenzoyl)-1,4,5-tris(hydroxymethyl)cyclopentane-1,3-diol 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: 83.0%

(1S,3R,4S,5R)-1,6:7,8-bis-O-isopropylidene-1,4,5-tris(hydroxymethyl)cyclopentane-1,3-diol (442906-60-7) + 4-nitro-benzoic acid (62-23-7) → (1S,4S,5R)-1,6:7,8-bis-O-isopropylidene-1,4,5-tris(hydroxymethyl)cyclopent-2-enol + (1S,3S,4S,5R)-1,6:7,8-bis-O-isopropylidene-3-(4'-nitrobenzoyl)-1,4,5-tris(hydroxymethyl)cyclopentane-1,3-diol (442906-69-6)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 0 - 20 ℃; for 17h;

DOI:10.1081/NCN-120006528

Reference yield:

(5S,7R,8S,9R)-8,9-Bis-hydroxymethyl-2,2-dimethyl-1,3-dioxa-spiro[4.4]nonan-7-ol (202402-54-8) → (1S,3S,4S,5R)-1,6:7,8-bis-O-isopropylidene-3-(4'-nitrobenzoyl)-1,4,5-tris(hydroxymethyl)cyclopentane-1,3-diol (442906-69-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / pyridinium p-toluenesulphonate; CuSO₄ / acetone / 1 h / 20 °C

2: 83 percent / PPh₃; diethyl azodicarboxylate / tetrahydrofuran / 17 h / 0 - 20 °C

With pyridinium p-toluenesulfonate; copper(II) sulfate; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; acetone; 2: Mitsunobu reaction;

DOI:10.1081/NCN-120006528

Reference yield:

(1S,3S,4S,5R)-1,6:7,8-bis-O-isopropylidene-3-(4'-nitrobenzoyl)-1,4,5-tris(hydroxymethyl)cyclopentane-1,3-diol (442906-69-6) → N-[9-(4-hydroxy-2,3,4-tris-hydroxymethyl-cyclopentyl)-9H-purin-6-yl]-benzamide

Guidance literature:

Multi-step reaction with 5 steps

1: 96 percent / NaOMe / methanol / 1 h / 20 °C

2: 17 percent / PPh₃; diethyl azodicarboxylate / tetrahydrofuran / 23.5 h / 4 - 20 °C

3: 89 percent / NH₃ / tetrahydrofuran / 72 h / 60 °C

4: 79 percent / pyridine / 2 h / 0 - 20 °C

5: aq. HCl / methanol / 6.5 h / 20 °C

With pyridine; hydrogenchloride; ammonia; sodium methylate; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; 2: Mitsunobu reaction;

DOI:10.1081/NCN-120006528

upstream raw materials:

(1S,3R,4S,5R)-1,6:7,8-bis-O-isopropylidene-1,4,5-tris(hydroxymethyl)cyclopentane-1,3-diol

4-nitro-benzoic acid

(5S,7R,8S,9R)-8,9-Bis-hydroxymethyl-2,2-dimethyl-1,3-dioxa-spiro[4.4]nonan-7-ol

Downstream raw materials:

C₂₆H₃₁N₅O₅

(1S,2R,3R,4R)-6,7,8-tri-O-acetyl-4-(6-benzamidopurin-9-yl)-1,2,3-tris(hydroxymethyl)cyclopentanol