(2R^*,3R^*,4R^*,5S^*)-6-benzyloxy-2-hydroxy-5-iodo-3-methyl-4-hexanolide

Base Information

• Chemical Name: (2R^*,3R^*,4R^*,5S^*)-6-benzyloxy-2-hydroxy-5-iodo-3-methyl-4-hexanolide
• CAS No.: 143729-24-2
• Molecular Formula: C₁₄H₁₇IO₄
• Molecular Weight: 376.191
• Mol file: 143729-24-2.mol

Synonyms:

Chemical Property of (2R^*,3R^*,4R^*,5S^*)-6-benzyloxy-2-hydroxy-5-iodo-3-methyl-4-hexanolide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R^*,3R^*,4R^*,5S^*)-6-benzyloxy-2-hydroxy-5-iodo-3-methyl-4-hexanolide

There total 1 articles about (2R^*,3R^*,4R^*,5S^*)-6-benzyloxy-2-hydroxy-5-iodo-3-methyl-4-hexanolide 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:

isoprpyl (2R*,3S*,4E)-6-benzyloxy-2-hydroxy-3-methyl-4-hexenoate (120506-06-1,120575-89-5,120575-90-8,120575-91-9,120575-92-0,121570-18-1,143729-26-4,143729-27-5,143729-28-6) → (2R*,3R*,4R*,5S*)-6-benzyloxy-2-hydroxy-5-iodo-3-methyl-4-hexanolide (137532-03-7,143729-24-2)

Guidance literature:

With potassium hydroxide; iodine; Yield given. Multistep reaction; 1.) methanol, RT, 1 d, 2.) acetonitrile, 0 deg C, 18 h;

DOI:10.1246/bcsj.65.1841

Reference yield: 90.0%

methanol (67-56-1) + (2R*,3R*,4R*,5S*)-6-benzyloxy-2-hydroxy-5-iodo-3-methyl-4-hexanolide (137532-03-7,143729-24-2) → methyl(2R*,3R*,4R*,5R*)-6-benzyloxy-4,5-epoxy-2-hydroxy-3-methylhexanoate (121485-05-0)

Guidance literature:

With sodium carbonate; for 48h; Ambient temperature;

DOI:10.1246/bcsj.65.1841

Reference yield:

(2R*,3R*,4R*,5S*)-6-benzyloxy-2-hydroxy-5-iodo-3-methyl-4-hexanolide (137532-03-7,143729-24-2) → (2R*)-2-<(1S*,4RS*,5S*,6R*,7R*)-4-(p-methoxybenzyloxy)-1,2,6-trimethyl-8,9-dioxabicyclo<3.3.1>non-2-en-7-yl>-1-propanol (143661-44-3,143729-29-7)

Guidance literature:

Multi-step reaction with 16 steps

1: 90 percent / Na₂CO₃ / 48 h / Ambient temperature

2: 99 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 6 h / Ambient temperature

3: 85 percent / lithium aluminum hydride / tetrahydrofuran / 1 h / -78 °C

4: 99 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 12 h / Ambient temperature

5: 99 percent / H₂ / 10percent Pd/C / ethanol / 8 h

6: 1.) Me₂S complex of copper(I) iodide / 1.) ether, -30 deg C, 2.) ether, 5 deg C, 13 h

7: 89 percent / pyridinium p-toluenesulfonate / benzene / 12 h / Ambient temperature

8: 99 percent / 1 M aq. KOH / methanol / 20 h / Ambient temperature

9: 97 percent / dimethyl sulfoxide, oxalyl chloride / CH₂Cl₂ / 0.17 h / -60 °C

10: 1.) BuLi / 1.) THF, hexane, -20 deg C, 20 min, 2.) THF, hexane, a) -20 deg C, 2 h, b) 5 deg C, 40 h

11: 63 percent / NaH / tetrahydrofuran; dimethylformamide / 16 h / Ambient temperature

12: 55 percent / methyl iodide, calcium carbonate / acetonitrile; H₂O / 40 h / Ambient temperature

13: 1.) sodium hydride / 1.) ether, RT, 1 h, 2.) ether, -20 deg C, 12 h

14: 87 percent / 1 M aq. KOH / methanol / 48 h / Ambient temperature

15: 79 percent / diethyl ether / 1 h / Ambient temperature

16: 57 percent / pyridinium p-toluenesulfonate / methanol / 20 h / Ambient temperature

With dmap; potassium hydroxide; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; copper(I) iodide dimethyl sulfide complex; hydrogen; pyridinium p-toluenesulfonate; sodium hydride; sodium carbonate; dimethyl sulfoxide; calcium carbonate; methyl iodide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; benzene;

DOI:10.1246/bcsj.65.1841

upstream raw materials:

isoprpyl (2R^*,3S^*,4E)-6-benzyloxy-2-hydroxy-3-methyl-4-hexenoate

Downstream raw materials:

methyl(2R^*,3R^*,4R^*,5R^*)-6-benzyloxy-4,5-epoxy-2-hydroxy-3-methylhexanoate

(2R^*,3S^*,4R^*,5R^*)-6-benzyloxy-4,5-epoxy-3-methyl-2-(2-tetrahydropyranyloxy)-1-hexanol

(2R^*)-2-<(1S^*,4RS^*,5S^*,6R^*,7R^*)-4-(p-methoxybenzyloxy)-1,2,6-trimethyl-8,9-dioxabicyclo<3.3.1>non-2-en-7-yl>-1-propanol

methyl (2R^*,3S^*,4R^*,5R^*)-6-benzyloxy-4,5-epoxy-3-methyl-2-(2-tetrahydropyranyloxy)hexanoate