(4R,5R,6R)-methyl5-(benzyloxy)-2,4,6-trimethyl-7-(trityloxy)-(E)-hept-2-enoate

Base Information

Chemical Name:(4R,5R,6R)-methyl5-(benzyloxy)-2,4,6-trimethyl-7-(trityloxy)-(E)-hept-2-enoate
CAS No.:108817-31-8
Molecular Formula:C₃₇H₄₀O₄
Molecular Weight:548.722
Hs Code.:

Synonyms:(4R,5R,6R)-methyl5-(benzyloxy)-2,4,6-trimethyl-7-(trityloxy)-(E)-hept-2-enoate

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Chemical Property of (4R,5R,6R)-methyl5-(benzyloxy)-2,4,6-trimethyl-7-(trityloxy)-(E)-hept-2-enoate

Chemical Property:

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Technology Process of (4R,5R,6R)-methyl5-(benzyloxy)-2,4,6-trimethyl-7-(trityloxy)-(E)-hept-2-enoate

There total 8 articles about (4R,5R,6R)-methyl5-(benzyloxy)-2,4,6-trimethyl-7-(trityloxy)-(E)-hept-2-enoate 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: 52.0%

: (α-carbomethoxyethylidene)triphenylphosphorane

: 108817-30-7
(2S,3R,4S)-3-(benzyloxy)-2,4-dimethyl-5-(trityloxy)pentanal

: 108817-31-8
(4R,5R,6R)-methyl5-(benzyloxy)-2,4,6-trimethyl-7-(trityloxy)-(E)-hept-2-enoate

Guidance literature:: In tetrahydrofuran; at 22 ℃; for 24h;
DOI:10.1021/jo00226a011

Reference yield:

: 88424-94-6
(1R,2R)-2-methyl-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-ol

: 108817-31-8
(4R,5R,6R)-methyl5-(benzyloxy)-2,4,6-trimethyl-7-(trityloxy)-(E)-hept-2-enoate

Guidance literature:: Multi-step reaction with 8 steps

1: 93 percent / DMAP / pyridine / 2 h / Ambient temperature

2: trifluoroacetic acid / methanol; H₂O / 48 h / Ambient temperature

3: 64 percent / NaOCH₃ / methanol / 0.5 h / 22 °C

4: 71 percent / CuCN / diethyl ether / 15 h / Ambient temperature

5: 93 percent / DMAP / pyridine / 5 h / 22 °C

6: 90 percent / NaH / dimethylformamide / 22 h / 50 °C

7: 1.) O₃, 2.) dimethyl sulfide / 1.) MeOH, -78 deg C, 2.) MeOH, 30 min

8: 52 percent / tetrahydrofuran / 24 h / 22 °C

With dmap; dimethylsulfide; sodium methylate; sodium hydride; ozone; trifluoroacetic acid; In tetrahydrofuran; pyridine; methanol; diethyl ether; water; N,N-dimethyl-formamide;
DOI:10.1021/jo00226a011

Reference yield:

: 108867-45-4
(2S,3S,4R)-2,4-dimethyl-hex-5-ene-1,3-diol

: 108817-31-8
(4R,5R,6R)-methyl5-(benzyloxy)-2,4,6-trimethyl-7-(trityloxy)-(E)-hept-2-enoate

Guidance literature:: Multi-step reaction with 4 steps

1: 93 percent / DMAP / pyridine / 5 h / 22 °C

2: 90 percent / NaH / dimethylformamide / 22 h / 50 °C

3: 1.) O₃, 2.) dimethyl sulfide / 1.) MeOH, -78 deg C, 2.) MeOH, 30 min

4: 52 percent / tetrahydrofuran / 24 h / 22 °C

With dmap; dimethylsulfide; sodium hydride; ozone; In tetrahydrofuran; pyridine; N,N-dimethyl-formamide;
DOI:10.1021/jo00226a011