Benzoic acid (1S,2R,3R)-2-benzyloxycarbonyl-3-hydroxymethyl-2,3-dimethyl-cyclopentylmethyl ester

Base Information

• Chemical Name: Benzoic acid (1S,2R,3R)-2-benzyloxycarbonyl-3-hydroxymethyl-2,3-dimethyl-cyclopentylmethyl ester
• CAS No.: 218271-70-6
• Molecular Formula: C₂₄H₂₈O₅
• Molecular Weight: 396.483

Synonyms:Benzoic acid (1S,2R,3R)-2-benzyloxycarbonyl-3-hydroxymethyl-2,3-dimethyl-cyclopentylmethyl ester

Chemical Property of Benzoic acid (1S,2R,3R)-2-benzyloxycarbonyl-3-hydroxymethyl-2,3-dimethyl-cyclopentylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of Benzoic acid (1S,2R,3R)-2-benzyloxycarbonyl-3-hydroxymethyl-2,3-dimethyl-cyclopentylmethyl ester

There total 10 articles about Benzoic acid (1S,2R,3R)-2-benzyloxycarbonyl-3-hydroxymethyl-2,3-dimethyl-cyclopentylmethyl 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: 44.0%

benzoyl chloride (98-88-4) + (1R,2R,5S)-2,5-Bis-hydroxymethyl-1,2-dimethyl-cyclopentanecarboxylic acid benzyl ester (218271-69-3) → Benzoic acid (1S,2R,3R)-2-benzyloxycarbonyl-3-hydroxymethyl-2,3-dimethyl-cyclopentylmethyl ester (218271-70-6)

Guidance literature:

With dmap; In dichloromethane; at -40 ℃;

DOI:10.1016/S0040-4039(98)01910-8

Reference yield:

(1R,4R,7R)-9-bromocamphor (10293-09-1) → Benzoic acid (1S,2R,3R)-2-benzyloxycarbonyl-3-hydroxymethyl-2,3-dimethyl-cyclopentylmethyl ester (218271-70-6)

Guidance literature:

Multi-step reaction with 9 steps

1: 96 percent / dimethylformamide / 110 °C

2: 93 percent / LiOH / tetrahydrofuran; H₂O / Ambient temperature

3: 80 percent / CrO₃, MnSO₄, aq. H₂SO₄

4: 87 percent / DBU / acetonitrile / Ambient temperature

5: 80 percent / SeO₂ / acetic anhydride / 145 °C

6: 74 percent / NaBH₄ / aq. ethanol / Ambient temperature

7: H₅IO₆ / tetrahydrofuran / Ambient temperature

8: NaBH₄ / aq. ethanol / Ambient temperature

9: 44 percent / DMAP / CH₂Cl₂ / -40 °C

With chromium(VI) oxide; dmap; lithium hydroxide; sodium tetrahydroborate; manganese(II) sulfate; selenium(IV) oxide; sulfuric acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; periodic acid; In tetrahydrofuran; ethanol; dichloromethane; water; acetic anhydride; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0040-4039(98)01910-8

Reference yield:

3-endo-9-dibromo-1,7,7-trimethylbicyclo<2.2.1>heptan-2-one (10293-10-4) → Benzoic acid (1S,2R,3R)-2-benzyloxycarbonyl-3-hydroxymethyl-2,3-dimethyl-cyclopentylmethyl ester (218271-70-6)

Guidance literature:

Multi-step reaction with 10 steps

1: 90 percent / Zn / acetic acid / Ambient temperature

2: 96 percent / dimethylformamide / 110 °C

3: 93 percent / LiOH / tetrahydrofuran; H₂O / Ambient temperature

4: 80 percent / CrO₃, MnSO₄, aq. H₂SO₄

5: 87 percent / DBU / acetonitrile / Ambient temperature

6: 80 percent / SeO₂ / acetic anhydride / 145 °C

7: 74 percent / NaBH₄ / aq. ethanol / Ambient temperature

8: H₅IO₆ / tetrahydrofuran / Ambient temperature

9: NaBH₄ / aq. ethanol / Ambient temperature

10: 44 percent / DMAP / CH₂Cl₂ / -40 °C

With chromium(VI) oxide; dmap; lithium hydroxide; sodium tetrahydroborate; manganese(II) sulfate; selenium(IV) oxide; sulfuric acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; periodic acid; zinc; In tetrahydrofuran; ethanol; dichloromethane; water; acetic anhydride; acetic acid; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0040-4039(98)01910-8

upstream raw materials:

benzoyl chloride

(1R,2R,5S)-2,5-Bis-hydroxymethyl-1,2-dimethyl-cyclopentanecarboxylic acid benzyl ester

(1R,4R,7R)-9-bromocamphor

3-endo-9-dibromo-1,7,7-trimethylbicyclo<2.2.1>heptan-2-one

Downstream raw materials:

Benzoic acid (1S,2R,3R)-2-benzyloxycarbonyl-3-(tert-butyl-diphenyl-silanyloxymethyl)-2,3-dimethyl-cyclopentylmethyl ester

(1R,2R,5S)-2-Formyl-5-hydroxymethyl-1,2-dimethyl-cyclopentanecarboxylic acid benzyl ester

Benzoic acid (1S,2R,3R)-2-benzyloxycarbonyl-3-formyl-2,3-dimethyl-cyclopentylmethyl ester

(1R,2R,5S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-1,2-dimethyl-5-((3aR,4R,6R,7aS)-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxymethyl)-cyclopentanecarboxylic acid benzyl ester

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