(1S,2R,3S,4S,5R)-2,3-Bis-benzyloxy-4,5-bis-(4-methoxy-benzyloxy)-cyclopentanecarbaldehyde

Base Information

• Chemical Name: (1S,2R,3S,4S,5R)-2,3-Bis-benzyloxy-4,5-bis-(4-methoxy-benzyloxy)-cyclopentanecarbaldehyde
• CAS No.: 1053735-44-6
• Molecular Formula: C₃₆H₃₈O₇
• Molecular Weight: 582.694
• Mol file: 1053735-44-6.mol

Synonyms:

Chemical Property of (1S,2R,3S,4S,5R)-2,3-Bis-benzyloxy-4,5-bis-(4-methoxy-benzyloxy)-cyclopentanecarbaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2R,3S,4S,5R)-2,3-Bis-benzyloxy-4,5-bis-(4-methoxy-benzyloxy)-cyclopentanecarbaldehyde

There total 11 articles about (1S,2R,3S,4S,5R)-2,3-Bis-benzyloxy-4,5-bis-(4-methoxy-benzyloxy)-cyclopentanecarbaldehyde 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:

methyl 4,6-O-para-methoxybenzylidene-α-D-glucopyranoside (18929-63-0) → (1S,2R,3S,4S,5R)-2,3-Bis-benzyloxy-4,5-bis-(4-methoxy-benzyloxy)-cyclopentanecarbaldehyde (1053735-44-6)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) dibutyltin oxide, tetrabutylammonium iodide / 1.) MeCN, reflux, 2 h, 2.) MeCN, reflux, 16 h

2: 87 percent / NaH / dimethylformamide / 3 h / Ambient temperature

3: 1.) LiAlH₄, 2.) AlCl₃ / 1.) THF, reflux, 1 h, 2.) THF, reflux, 2.5 h

4: 1.) DMSO, oxalyl chloride, 2.) triethylamine / 1.) CH₂Cl₂, -60 deg C, 20 min, 2.) CH₂Cl₂, -60 deg C, 10 min

5: 86 percent / potassium tert-butoxide / tetrahydrofuran / 1 h / Ambient temperature

6: 1.) zirconocene dichloride, n-BuLi, 2.) BF₃*Et₂O / 1.) THF, room temp., 3 h, 2.) THF, room temp., 30 min

7: NaH / dimethylformamide

8: OsO₄, NaIO₄ / diethyl ether / 24 h / Ambient temperature

With sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; n-butyllithium; aluminium trichloride; oxalyl dichloride; zirconocene dichloride; boron trifluoride diethyl etherate; potassium tert-butylate; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide;

DOI:10.1021/jo961158y

Reference yield:

p-Anisaldehyde dimethyl acetal (2186-92-7) → (1S,2R,3S,4S,5R)-2,3-Bis-benzyloxy-4,5-bis-(4-methoxy-benzyloxy)-cyclopentanecarbaldehyde (1053735-44-6)

Guidance literature:

Multi-step reaction with 9 steps

1: 84 percent / p-toluenesulfonic acid / dimethylformamide / 4 h / 70 °C

2: 1.) dibutyltin oxide, tetrabutylammonium iodide / 1.) MeCN, reflux, 2 h, 2.) MeCN, reflux, 16 h

3: 87 percent / NaH / dimethylformamide / 3 h / Ambient temperature

4: 1.) LiAlH₄, 2.) AlCl₃ / 1.) THF, reflux, 1 h, 2.) THF, reflux, 2.5 h

5: 1.) DMSO, oxalyl chloride, 2.) triethylamine / 1.) CH₂Cl₂, -60 deg C, 20 min, 2.) CH₂Cl₂, -60 deg C, 10 min

6: 86 percent / potassium tert-butoxide / tetrahydrofuran / 1 h / Ambient temperature

7: 1.) zirconocene dichloride, n-BuLi, 2.) BF₃*Et₂O / 1.) THF, room temp., 3 h, 2.) THF, room temp., 30 min

8: NaH / dimethylformamide

9: OsO₄, NaIO₄ / diethyl ether / 24 h / Ambient temperature

With sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; n-butyllithium; aluminium trichloride; oxalyl dichloride; zirconocene dichloride; boron trifluoride diethyl etherate; potassium tert-butylate; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide;

DOI:10.1021/jo961158y

Reference yield:

p-methoxybenzyl chloride (824-94-2) → (1S,2R,3S,4S,5R)-2,3-Bis-benzyloxy-4,5-bis-(4-methoxy-benzyloxy)-cyclopentanecarbaldehyde (1053735-44-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 87 percent / NaH / dimethylformamide / 3 h / Ambient temperature

2: 1.) LiAlH₄, 2.) AlCl₃ / 1.) THF, reflux, 1 h, 2.) THF, reflux, 2.5 h

3: 1.) DMSO, oxalyl chloride, 2.) triethylamine / 1.) CH₂Cl₂, -60 deg C, 20 min, 2.) CH₂Cl₂, -60 deg C, 10 min

4: 86 percent / potassium tert-butoxide / tetrahydrofuran / 1 h / Ambient temperature

5: 1.) zirconocene dichloride, n-BuLi, 2.) BF₃*Et₂O / 1.) THF, room temp., 3 h, 2.) THF, room temp., 30 min

6: NaH / dimethylformamide

7: OsO₄, NaIO₄ / diethyl ether / 24 h / Ambient temperature

With sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; n-butyllithium; aluminium trichloride; oxalyl dichloride; zirconocene dichloride; boron trifluoride diethyl etherate; potassium tert-butylate; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide;

DOI:10.1021/jo961158y

upstream raw materials:

(1R,2S,3S,4R,5S)-3,4-bis(benzyloxy)-1,2-bis[(p-methoxybenzyl)oxy]-5-vinylcyclopentane

methyl 4,6-O-para-methoxybenzylidene-α-D-glucopyranoside

p-Anisaldehyde dimethyl acetal

p-methoxybenzyl chloride

Downstream raw materials:

Phosphoric acid dibenzyl ester (1R,2S,3R,4S,5R)-2,3-bis-benzyloxy-5-(bis-benzyloxy-phosphoryloxy)-4-(bis-benzyloxy-phosphoryloxymethyl)-cyclopentyl ester

(1R,2S,3R,4R,5R)-3,4-Bis-benzyloxy-5-hydroxymethyl-cyclopentane-1,2-diol