(3R,5R,6S,7S,9R,13R,14R)-14-ethyl-13-benzyloxy-6-(4-methoxybenzyloxy)-3,5,7,9,13-pentamethyl-1-oxacyclotetradec-11(E)-ene-2,4,10-trione

Base Information

• Chemical Name: (3R,5R,6S,7S,9R,13R,14R)-14-ethyl-13-benzyloxy-6-(4-methoxybenzyloxy)-3,5,7,9,13-pentamethyl-1-oxacyclotetradec-11(E)-ene-2,4,10-trione
• CAS No.: 102852-08-4
• Molecular Formula: C₃₅H₄₆O₇
• Molecular Weight: 578.746

Synonyms:(3R,5R,6S,7S,9R,13R,14R)-14-ethyl-13-benzyloxy-6-(4-methoxybenzyloxy)-3,5,7,9,13-pentamethyl-1-oxacyclotetradec-11(E)-ene-2,4,10-trione

Chemical Property of (3R,5R,6S,7S,9R,13R,14R)-14-ethyl-13-benzyloxy-6-(4-methoxybenzyloxy)-3,5,7,9,13-pentamethyl-1-oxacyclotetradec-11(E)-ene-2,4,10-trione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,5R,6S,7S,9R,13R,14R)-14-ethyl-13-benzyloxy-6-(4-methoxybenzyloxy)-3,5,7,9,13-pentamethyl-1-oxacyclotetradec-11(E)-ene-2,4,10-trione

There total 22 articles about (3R,5R,6S,7S,9R,13R,14R)-14-ethyl-13-benzyloxy-6-(4-methoxybenzyloxy)-3,5,7,9,13-pentamethyl-1-oxacyclotetradec-11(E)-ene-2,4,10-trione 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:

(3S,4R,5S)-4-hydroxy-5(2(S)-isopropyloxy-3(R),5(S)-dimethyl-6(S)-tetrahydroxypropanyl)-3-methylhexane (102851-96-7) → (3R,5R,6S,7S,9R,13R,14R)-14-ethyl-13-benzyloxy-6-(4-methoxybenzyloxy)-3,5,7,9,13-pentamethyl-1-oxacyclotetradec-11(E)-ene-2,4,10-trione (102852-08-4)

Guidance literature:

Multi-step reaction with 15 steps

1: 95 percent / KCH₂S(O)Me / Ambient temperature

2: 1.) 1 N HCl; 2.) Ca(BH₄)2 / 1.) THF, 50 deg C, 12 h; 2.) EtOH, rt, 3 h

3: CSA / 0.5 h / Ambient temperature

4: KCH₂S(O)Me / dimethylsulfoxide / Ambient temperature

5: 1 N HCl

6: 95 percent / Me₂SO, (COCl)2, Et₃N / CH₂Cl₂

7: 91 percent / n-BuLi / tetrahydrofuran / -80 °C

8: 87 percent / PDC / dimethylformamide

9: 74 percent / OsO₄, NMO / acetone; H₂O

10: 100 percent / NaIO₄

11: 72 percent / CrO₃, H₂SO₄ / acetone / 0.08 h / -20 °C

12: 60 percent / 2,4,6-Cl₃C₆H₂COCl, Et₃N, DMAP / tetrahydrofuran; toluene / 1 h / Ambient temperature

13: 89 percent / K₂CO₃, 18-crown-6 / toluene / 1 h / 80 °C

14: 42 percent / DDQ / toluene; H₂O / 4.5 h / 0 °C

15: 91 percent / Me₂SO, (COCl)2, Et₃N / CH₂Cl₂ / -50 °C

With chromium(VI) oxide; hydrogenchloride; dmap; sodium periodate; osmium(VIII) oxide; dipyridinium dichromate; n-butyllithium; N-methyl-2-indolinone; calcium borohydride; oxalyl dichloride; 18-crown-6 ether; sulfuric acid; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; potassium dimsylate; potassium carbonate; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1021/ja00275a063

Reference yield:

(3S,4R,5S)-4-(3,4-dimethoxybenzyloxy)-5-<2(S)-isopropyloxy-3(R),5(S)-dimethyl-6(S)-tetrahydroxypyranyl>-3-methylhexane (102851-97-8) → (3R,5R,6S,7S,9R,13R,14R)-14-ethyl-13-benzyloxy-6-(4-methoxybenzyloxy)-3,5,7,9,13-pentamethyl-1-oxacyclotetradec-11(E)-ene-2,4,10-trione (102852-08-4)

Guidance literature:

Multi-step reaction with 14 steps

1: 1.) 1 N HCl; 2.) Ca(BH₄)2 / 1.) THF, 50 deg C, 12 h; 2.) EtOH, rt, 3 h

2: CSA / 0.5 h / Ambient temperature

3: KCH₂S(O)Me / dimethylsulfoxide / Ambient temperature

4: 1 N HCl

5: 95 percent / Me₂SO, (COCl)2, Et₃N / CH₂Cl₂

6: 91 percent / n-BuLi / tetrahydrofuran / -80 °C

7: 87 percent / PDC / dimethylformamide

8: 74 percent / OsO₄, NMO / acetone; H₂O

9: 100 percent / NaIO₄

10: 72 percent / CrO₃, H₂SO₄ / acetone / 0.08 h / -20 °C

11: 60 percent / 2,4,6-Cl₃C₆H₂COCl, Et₃N, DMAP / tetrahydrofuran; toluene / 1 h / Ambient temperature

12: 89 percent / K₂CO₃, 18-crown-6 / toluene / 1 h / 80 °C

13: 42 percent / DDQ / toluene; H₂O / 4.5 h / 0 °C

14: 91 percent / Me₂SO, (COCl)2, Et₃N / CH₂Cl₂ / -50 °C

With chromium(VI) oxide; hydrogenchloride; dmap; sodium periodate; osmium(VIII) oxide; dipyridinium dichromate; n-butyllithium; N-methyl-2-indolinone; calcium borohydride; oxalyl dichloride; 18-crown-6 ether; sulfuric acid; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; potassium dimsylate; potassium carbonate; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1021/ja00275a063

Reference yield:

(2R,4S,5S,6R,7R,8S)-7-(3,4-dimethoxybenzyloxy)-5-(4-methoxybenzyloxy)-2,4,6,8-tetramethyl-9-hexenal (102852-02-8) → (3R,5R,6S,7S,9R,13R,14R)-14-ethyl-13-benzyloxy-6-(4-methoxybenzyloxy)-3,5,7,9,13-pentamethyl-1-oxacyclotetradec-11(E)-ene-2,4,10-trione (102852-08-4)

Guidance literature:

Multi-step reaction with 9 steps

1: 91 percent / n-BuLi / tetrahydrofuran / -80 °C

2: 87 percent / PDC / dimethylformamide

3: 74 percent / OsO₄, NMO / acetone; H₂O

4: 100 percent / NaIO₄

5: 72 percent / CrO₃, H₂SO₄ / acetone / 0.08 h / -20 °C

6: 60 percent / 2,4,6-Cl₃C₆H₂COCl, Et₃N, DMAP / tetrahydrofuran; toluene / 1 h / Ambient temperature

7: 89 percent / K₂CO₃, 18-crown-6 / toluene / 1 h / 80 °C

8: 42 percent / DDQ / toluene; H₂O / 4.5 h / 0 °C

9: 91 percent / Me₂SO, (COCl)2, Et₃N / CH₂Cl₂ / -50 °C

With chromium(VI) oxide; dmap; sodium periodate; osmium(VIII) oxide; dipyridinium dichromate; n-butyllithium; N-methyl-2-indolinone; oxalyl dichloride; 18-crown-6 ether; sulfuric acid; 2,4,6-trichlorobenzoyl chloride; potassium carbonate; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1021/ja00275a063

upstream raw materials:

(3R,4S,5R,6S,7S,9R,13R,14R)-13-benzyloxy-4-(3,4-dimethoxybenzyloxy)-14-ethyl-6-(4-methoxybenzyloxy)-3,5,7,9,13-pentamethyl-1-oxacyclotetradec-11(E)-ene-2,10-dione

(2S,3R,5S,6S)-2-isopropyloxy-3,5-dimethyl-6-<1(S)-methyl-2-hydroxyethyl>tetrahydropyran

(R)-2-((2S,3S,5R,6S)-6-Isopropoxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-propionaldehyde

(3S,4R,5S)-4-hydroxy-5(2(S)-isopropyloxy-3(R),5(S)-dimethyl-6(S)-tetrahydroxypropanyl)-3-methylhexane

Downstream raw materials:

pikronolide

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