<4R,4(2S,3S,5R),5<(2RS,3R,5R),5(1S)>>-4-<5-<5-(1-benzyloxy)propyl-5-ethyl-2-methoxy-3-methyltetrahydrofuran-2-yl>-3,5-dimethyltetrahydrofuran-2-yl>hexan-3-one

Base Information

Chemical Name:<4R,4(2S,3S,5R),5<(2RS,3R,5R),5(1S)>>-4-<5-<5-(1-benzyloxy)propyl-5-ethyl-2-methoxy-3-methyltetrahydrofuran-2-yl>-3,5-dimethyltetrahydrofuran-2-yl>hexan-3-one
CAS No.:144535-03-5
Molecular Formula:C₃₀H₄₈O₅
Molecular Weight:488.708
Hs Code.:

<4R,4(2S,3S,5R),5<(2RS,3R,5R),5(1S)>>-4-<5-<5-(1-benzyloxy)propyl-5-ethyl-2-methoxy-3-methyltetrahydrofuran-2-yl>-3,5-dimethyltetrahydrofuran-2-yl>hexan-3-one

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Chemical Property of <4R,4(2S,3S,5R),5<(2RS,3R,5R),5(1S)>>-4-<5-<5-(1-benzyloxy)propyl-5-ethyl-2-methoxy-3-methyltetrahydrofuran-2-yl>-3,5-dimethyltetrahydrofuran-2-yl>hexan-3-one

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Technology Process of <4R,4(2S,3S,5R),5<(2RS,3R,5R),5(1S)>>-4-<5-<5-(1-benzyloxy)propyl-5-ethyl-2-methoxy-3-methyltetrahydrofuran-2-yl>-3,5-dimethyltetrahydrofuran-2-yl>hexan-3-one

There total 46 articles about <4R,4(2S,3S,5R),5<(2RS,3R,5R),5(1S)>>-4-<5-<5-(1-benzyloxy)propyl-5-ethyl-2-methoxy-3-methyltetrahydrofuran-2-yl>-3,5-dimethyltetrahydrofuran-2-yl>hexan-3-one 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: 98.0%

: 67-56-1
methanol

: 144535-02-4
<4R,4(2S,3S,5R),5<(2R,3R,5R),5(1S)>>-4-<5-<5-(1-benzyloxy)propyl-5-ethyl-2-hydroxy-3-methyltetrahydrofuran-2-yl>-3,5-dimethyltetrahydrofuran-2-yl>hexan-3-one

: 144535-03-5,144606-51-9
<4R,4(2S,3S,5R),5<(2RS,3R,5R),5(1S)>>-4-<5-<5-(1-benzyloxy)propyl-5-ethyl-2-methoxy-3-methyltetrahydrofuran-2-yl>-3,5-dimethyltetrahydrofuran-2-yl>hexan-3-one

Guidance literature:: With camphor-10-sulfonic acid; for 0.5h; Ambient temperature;
DOI:10.1016/0040-4020(95)00906-X

Reference yield: 77.0%

: <3R,4RS,4(2S,3S,5R),5<(2RS,3R,5S),5(1R)>>-4-<5-<5-(1-benzyloxy)propyl-5-ethyl-2-methoxy-3-methyltetrahydrofuran-2-yl>-3,5-dimethyltetrahydrofuran-2-yl>hexan-3-ol

: 144535-03-5,144606-51-9
<4R,4(2S,3S,5R),5<(2RS,3R,5R),5(1S)>>-4-<5-<5-(1-benzyloxy)propyl-5-ethyl-2-methoxy-3-methyltetrahydrofuran-2-yl>-3,5-dimethyltetrahydrofuran-2-yl>hexan-3-one

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; for 0.666667h;
DOI:10.1016/0040-4020(95)00906-X

Reference yield:

: (2S,3R,5R,6S)-6-benzyloxy-5-tert-butyldimethylsilyloxy-5-ethyl-2-(4-methoxybenzyloxy)-3-methyloctanal

: 144535-03-5,144606-51-9
<4R,4(2S,3S,5R),5<(2RS,3R,5R),5(1S)>>-4-<5-<5-(1-benzyloxy)propyl-5-ethyl-2-methoxy-3-methyltetrahydrofuran-2-yl>-3,5-dimethyltetrahydrofuran-2-yl>hexan-3-one

Guidance literature:: Multi-step reaction with 17 steps

1: 1.) n-BuLi / 1.) ether, hexane, 2 h, 2.) ether, hexane, -55 deg C, 2 h

2: oxalyl chloride, DMSO, Et₃N / CH₂Cl₂ / -78 - -30 °C

3: n-Bu₃SnH, 2,2-azobisisobutyronitrile / benzene / 5 h / 80 °C

4: 82 percent / diethyl ether / 2 h / -78 - -20 °C

5: 1.) 2,3-dichloro-5,6-dicyanobenzoquinone, 2.) LiAlH₄ / 1.) CH₂Cl₂, H₂O, 20 min, 2.) ether, 0 deg C, 1 h

6: 100 percent / pyridine / 10 h

7: 1N aq. H₂SO₄ / tetrahydrofuran / 24 h / Ambient temperature

8: K₂CO₃ / methanol / 1 h

9: (+/-)-10-camphorsulfonic acid / CH₂Cl₂ / 0.5 h / Ambient temperature

10: 93 percent / imidazole / CH₂Cl₂ / 1 h / Ambient temperature

11: 96 percent / Et₃N, DMAP / CH₂Cl₂ / 0.33 h / Ambient temperature

12: 97 percent / 1N aq. HCl / 4 h / Ambient temperature

13: 97 percent / oxalyl chloride, DMSO / CH₂Cl₂ / -78 °C

14: 75 percent / tetrahydrofuran / 2 h / -78 - -20 °C

15: 90 percent / n-Bu₄NF / dimethylformamide; tetrahydrofuran / 4 h / Ambient temperature

16: 1.) pyridinium chlorochromate, molecular sieves 3A, 2.) 1N aq. H₂SO₄ / 1.) CH₂Cl₂, RT, 45 min, 2.) THF, 20 min

17: 98 percent / CSA / 0.5 h / Ambient temperature

With pyridine; 1H-imidazole; hydrogenchloride; dmap; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); 3 A molecular sieve; sulfuric acid; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1016/0040-4020(95)00906-X