(4S,6S)-4-((R)-2-Benzyloxy-1-methyl-ethyl)-6-((E)-1-methyl-propenyl)-2-phenylselanylmethyl-[1,3]dioxane

Base Information

• Chemical Name: (4S,6S)-4-((R)-2-Benzyloxy-1-methyl-ethyl)-6-((E)-1-methyl-propenyl)-2-phenylselanylmethyl-[1,3]dioxane
• CAS No.: 240485-16-9
• Molecular Formula: C₂₅H₃₂O₃Se
• Molecular Weight: 459.487

Synonyms:(4S,6S)-4-((R)-2-Benzyloxy-1-methyl-ethyl)-6-((E)-1-methyl-propenyl)-2-phenylselanylmethyl-[1,3]dioxane

Chemical Property of (4S,6S)-4-((R)-2-Benzyloxy-1-methyl-ethyl)-6-((E)-1-methyl-propenyl)-2-phenylselanylmethyl-[1,3]dioxane

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Technology Process of (4S,6S)-4-((R)-2-Benzyloxy-1-methyl-ethyl)-6-((E)-1-methyl-propenyl)-2-phenylselanylmethyl-[1,3]dioxane

There total 4 articles about (4S,6S)-4-((R)-2-Benzyloxy-1-methyl-ethyl)-6-((E)-1-methyl-propenyl)-2-phenylselanylmethyl-[1,3]dioxane 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%

2-phenylselenoacetaldehyde diethylacetal (71338-47-1) + (E)-(4S,6S,7R)-8-benzyloxy-3,7-dimethyl-oct-2-ene-4,6-diol (240485-12-5) → (4S,6S)-4-((R)-2-Benzyloxy-1-methyl-ethyl)-6-((E)-1-methyl-propenyl)-2-phenylselanylmethyl-[1,3]dioxane (240485-16-9)

Guidance literature:

With pyridinium p-toluenesulfonate; In toluene; at 110 ℃; for 18h;

DOI:10.1055/s-1999-3099

Reference yield:

2-methylbut-2-enal (497-03-0) → (4S,6S)-4-((R)-2-Benzyloxy-1-methyl-ethyl)-6-((E)-1-methyl-propenyl)-2-phenylselanylmethyl-[1,3]dioxane (240485-16-9)

Guidance literature:

Multi-step reaction with 3 steps

2: 66 percent / Me₄NHB(OAc)3, AcOH / acetonitrile / 18 h / -35 °C

3: 52 percent / PPTS / toluene / 18 h / 110 °C

With pyridinium p-toluenesulfonate; acetic acid; tetramethylammonium triacetoxyborohydride; In toluene; acetonitrile;

DOI:10.1055/s-1999-3099

Reference yield:

(-)-(R)-4-benzyloxy-3-methylbutan-2-one (82167-79-1) → (4S,6S)-4-((R)-2-Benzyloxy-1-methyl-ethyl)-6-((E)-1-methyl-propenyl)-2-phenylselanylmethyl-[1,3]dioxane (240485-16-9)

Guidance literature:

Multi-step reaction with 3 steps

2: 66 percent / Me₄NHB(OAc)3, AcOH / acetonitrile / 18 h / -35 °C

3: 52 percent / PPTS / toluene / 18 h / 110 °C

With pyridinium p-toluenesulfonate; acetic acid; tetramethylammonium triacetoxyborohydride; In toluene; acetonitrile;

DOI:10.1055/s-1999-3099

upstream raw materials:

2-phenylselenoacetaldehyde diethylacetal

(E)-(4S,6S,7R)-8-benzyloxy-3,7-dimethyl-oct-2-ene-4,6-diol

2-methylbut-2-enal

(-)-(R)-4-benzyloxy-3-methylbutan-2-one

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