[(1S,2R,3S,4S,5R)-2,3-Bis-benzyloxy-4,5-bis-(4-methoxy-benzyloxy)-cyclopentyl]-methanol

Base Information

Chemical Name:[(1S,2R,3S,4S,5R)-2,3-Bis-benzyloxy-4,5-bis-(4-methoxy-benzyloxy)-cyclopentyl]-methanol
CAS No.:183170-45-8
Molecular Formula:C₃₆H₄₀O₇
Molecular Weight:584.709
Hs Code.:

Synonyms:[(1S,2R,3S,4S,5R)-2,3-Bis-benzyloxy-4,5-bis-(4-methoxy-benzyloxy)-cyclopentyl]-methanol

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Chemical Property of [(1S,2R,3S,4S,5R)-2,3-Bis-benzyloxy-4,5-bis-(4-methoxy-benzyloxy)-cyclopentyl]-methanol

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Technology Process of [(1S,2R,3S,4S,5R)-2,3-Bis-benzyloxy-4,5-bis-(4-methoxy-benzyloxy)-cyclopentyl]-methanol

There total 11 articles about [(1S,2R,3S,4S,5R)-2,3-Bis-benzyloxy-4,5-bis-(4-methoxy-benzyloxy)-cyclopentyl]-methanol 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: 28.0%

: 100-39-0
benzyl bromide

: 183170-43-6
(1R,2S,3S,4R,5S)-2-Benzyloxy-5-hydroxymethyl-3,4-bis-(4-methoxy-benzyloxy)-cyclopentanol

: 183170-45-8
[(1S,2R,3S,4S,5R)-2,3-Bis-benzyloxy-4,5-bis-(4-methoxy-benzyloxy)-cyclopentyl]-methanol

: 183170-47-0
(1R,2S,3S,4R,5S)-2-Benzyloxy-5-benzyloxymethyl-3,4-bis-(4-methoxy-benzyloxy)-cyclopentanol

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 1h;
DOI:10.1021/jo961158y

Reference yield:

: 18929-63-0
methyl 4,6-O-para-methoxybenzylidene-α-D-glucopyranoside

: 183170-45-8
[(1S,2R,3S,4S,5R)-2,3-Bis-benzyloxy-4,5-bis-(4-methoxy-benzyloxy)-cyclopentyl]-methanol

Guidance literature:: Multi-step reaction with 9 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

9: NaBH₄ / methanol / 0.5 h

With sodium tetrahydroborate; 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; methanol; diethyl ether; N,N-dimethyl-formamide;
DOI:10.1021/jo961158y

Reference yield:

: 824-94-2
p-methoxybenzyl chloride

: 183170-45-8
[(1S,2R,3S,4S,5R)-2,3-Bis-benzyloxy-4,5-bis-(4-methoxy-benzyloxy)-cyclopentyl]-methanol

Guidance literature:: Multi-step reaction with 8 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

8: NaBH₄ / methanol / 0.5 h

With sodium tetrahydroborate; 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; methanol; diethyl ether; N,N-dimethyl-formamide;
DOI:10.1021/jo961158y