(2S,4R,6S)-1-(4'-fluoro-3,3',5-trimethyl<1,1'-biphenyl>-2-yl)-2-<4-(benzyloxy)-2-methoxy-3,4,5,6-tetrahydro-2H-pyran-6-yl>ethyl phenyl sulfoxide

Base Information

• Chemical Name: (2S,4R,6S)-1-(4'-fluoro-3,3',5-trimethyl<1,1'-biphenyl>-2-yl)-2-<4-(benzyloxy)-2-methoxy-3,4,5,6-tetrahydro-2H-pyran-6-yl>ethyl phenyl sulfoxide
• CAS No.: 100295-44-1
• Molecular Formula: C₃₆H₃₉FO₄S
• Molecular Weight: 586.768
• Mol file: 100295-44-1.mol

Synonyms:

Chemical Property of (2S,4R,6S)-1-(4'-fluoro-3,3',5-trimethyl<1,1'-biphenyl>-2-yl)-2-<4-(benzyloxy)-2-methoxy-3,4,5,6-tetrahydro-2H-pyran-6-yl>ethyl phenyl sulfoxide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4R,6S)-1-(4'-fluoro-3,3',5-trimethyl<1,1'-biphenyl>-2-yl)-2-<4-(benzyloxy)-2-methoxy-3,4,5,6-tetrahydro-2H-pyran-6-yl>ethyl phenyl sulfoxide

There total 17 articles about (2S,4R,6S)-1-(4'-fluoro-3,3',5-trimethyl<1,1'-biphenyl>-2-yl)-2-<4-(benzyloxy)-2-methoxy-3,4,5,6-tetrahydro-2H-pyran-6-yl>ethyl phenyl sulfoxide 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 3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-ribo-hexopyranoside (63592-79-0) → (2S,4R,6S)-1-(4'-fluoro-3,3',5-trimethyl<1,1'-biphenyl>-2-yl)-2-<4-(benzyloxy)-2-methoxy-3,4,5,6-tetrahydro-2H-pyran-6-yl>ethyl phenyl sulfoxide (90691-42-2,100295-44-1,100295-45-2)

Guidance literature:

Multi-step reaction with 8 steps

1: 88 percent / aq. trifluoroacetic acid / CH₂Cl₂ / 0.17 h

2: 86 percent / pyridine / 144 h

3: 89.5 percent / pyridine / Ambient temperature

4: 83.5 percent / 70percent aq. trifluoroacetic acid / CH₂Cl₂ / 0.08 h

5: 81.3 percent / NaBH₄ / dimethylsulfoxide / 96 h / 80 °C

6: 77.5 percent / pyridine / 4 h / Ambient temperature

7: 86 percent / NaI / acetone / 24 h / Heating

8: 1.) NaH / 1.) DMSO, RT, 10 min, 2.) DMSO, RT, 1 h

With pyridine; sodium tetrahydroborate; sodium hydride; trifluoroacetic acid; sodium iodide; In dichloromethane; dimethyl sulfoxide; acetone;

DOI:10.1021/jo00355a014

Reference yield:

methyl 3-O-benzyl-4-O-tosyl-2-deoxy-α-D-ribo-hexopyranoside (82300-41-2) → (2S,4R,6S)-1-(4'-fluoro-3,3',5-trimethyl<1,1'-biphenyl>-2-yl)-2-<4-(benzyloxy)-2-methoxy-3,4,5,6-tetrahydro-2H-pyran-6-yl>ethyl phenyl sulfoxide (90691-42-2,100295-44-1,100295-45-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 81.3 percent / NaBH₄ / dimethylsulfoxide / 96 h / 80 °C

2: 77.5 percent / pyridine / 4 h / Ambient temperature

3: 86 percent / NaI / acetone / 24 h / Heating

4: 1.) NaH / 1.) DMSO, RT, 10 min, 2.) DMSO, RT, 1 h

With pyridine; sodium tetrahydroborate; sodium hydride; sodium iodide; In dimethyl sulfoxide; acetone;

DOI:10.1021/jo00355a014

Reference yield:

methyl 3-O-benzyl-2-deoxy-α-D-ribo-hexopyranoside (64951-98-0) → (2S,4R,6S)-1-(4'-fluoro-3,3',5-trimethyl<1,1'-biphenyl>-2-yl)-2-<4-(benzyloxy)-2-methoxy-3,4,5,6-tetrahydro-2H-pyran-6-yl>ethyl phenyl sulfoxide (90691-42-2,100295-44-1,100295-45-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 86 percent / pyridine / 144 h

2: 89.5 percent / pyridine / Ambient temperature

3: 83.5 percent / 70percent aq. trifluoroacetic acid / CH₂Cl₂ / 0.08 h

4: 81.3 percent / NaBH₄ / dimethylsulfoxide / 96 h / 80 °C

5: 77.5 percent / pyridine / 4 h / Ambient temperature

6: 86 percent / NaI / acetone / 24 h / Heating

7: 1.) NaH / 1.) DMSO, RT, 10 min, 2.) DMSO, RT, 1 h

With pyridine; sodium tetrahydroborate; sodium hydride; trifluoroacetic acid; sodium iodide; In dichloromethane; dimethyl sulfoxide; acetone;

DOI:10.1021/jo00355a014

upstream raw materials:

methyl 3-O-benzyl-2,4,6-trideoxy-6-iodo-α-D-erythro-hexopyranoside

(4'-fluoro-3,3',5-trimethyl<1,1'-biphenyl>-2-yl)methyl phenyl sulfide

thiophenolate

2-(4-fluoro-3-methyl-phenyl)-4,6-dimethylbenzyl alcohol

Downstream raw materials:

(2S,4R,6S)-(E)-6-<2-(4'-fluoro-3,3',5-trimethyl<1,1'-biphenyl>-2-yl)ethenyl>-4-(benzyloxy)-2-methoxy-3,4,5,6-tetrahydro-2H-pyran

(2R,4R,6S)-(E)-6-<2-(4'-fluoro,3,3',5-trimethyl<1,1'-biphenyl>-2-yl)ethenyl>-4-(benzyloxy)-2-methoxy-3,4,5,6-tetrahydro-2H-pyran

Refernces

• 1、 Prugh,Rooney,Deana,Ramjit. "Utilization of the chiral synthon, methyl 3-0-benzyl-2,4,6-trideoxy-6-iodo-α-D-erythro-hexopyranoside in the synthesis of a potent HMG-CoA reductase inhibitor". . p. 2947 - 2950. Retrieved 2007/10/02.