(3aR,4S,6S,7S,7aR)-7-Benzyloxy-2,2,4-trimethyl-6-pent-4-enyloxy-tetrahydro-[1,3]dioxolo[4,5-c]pyran

Base Information

Chemical Name:(3aR,4S,6S,7S,7aR)-7-Benzyloxy-2,2,4-trimethyl-6-pent-4-enyloxy-tetrahydro-[1,3]dioxolo[4,5-c]pyran
CAS No.:373606-47-4
Molecular Formula:C₂₁H₃₀O₅
Molecular Weight:362.466
Hs Code.:

Synonyms:(3aR,4S,6S,7S,7aR)-7-Benzyloxy-2,2,4-trimethyl-6-pent-4-enyloxy-tetrahydro-[1,3]dioxolo[4,5-c]pyran

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Chemical Property of (3aR,4S,6S,7S,7aR)-7-Benzyloxy-2,2,4-trimethyl-6-pent-4-enyloxy-tetrahydro-[1,3]dioxolo[4,5-c]pyran

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Technology Process of (3aR,4S,6S,7S,7aR)-7-Benzyloxy-2,2,4-trimethyl-6-pent-4-enyloxy-tetrahydro-[1,3]dioxolo[4,5-c]pyran

There total 5 articles about (3aR,4S,6S,7S,7aR)-7-Benzyloxy-2,2,4-trimethyl-6-pent-4-enyloxy-tetrahydro-[1,3]dioxolo[4,5-c]pyran 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: 93.0%

: 100-39-0
benzyl bromide

: 143697-28-3
Pent-4-enyl 3,4-O-isopropylidene-β-L-fucopyranoside

: 373606-47-4
(3aR,4S,6S,7S,7aR)-7-Benzyloxy-2,2,4-trimethyl-6-pent-4-enyloxy-tetrahydro-[1,3]dioxolo[4,5-c]pyran

Guidance literature:: With tetra-(n-butyl)ammonium iodide; sodium hydride; In N,N-dimethyl-formamide;
DOI:10.1021/ja016227r

Reference yield:

: 143416-55-1
1-O-(4-pentenyl) β-L-fucopyranoside

: 373606-47-4
(3aR,4S,6S,7S,7aR)-7-Benzyloxy-2,2,4-trimethyl-6-pent-4-enyloxy-tetrahydro-[1,3]dioxolo[4,5-c]pyran

Guidance literature:: Multi-step reaction with 2 steps

1: p-TsOH

2: 93 percent / NaH; TBAI / dimethylformamide

With tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; In N,N-dimethyl-formamide;
DOI:10.1021/ja016227r

Reference yield:

: 16741-27-8
2,3,4-tri-O-acetyl-α-L-fucopyranosyl bromide

: 373606-47-4
(3aR,4S,6S,7S,7aR)-7-Benzyloxy-2,2,4-trimethyl-6-pent-4-enyloxy-tetrahydro-[1,3]dioxolo[4,5-c]pyran

Guidance literature:: Multi-step reaction with 4 steps

1: MS; Ag₂CO₃

2: 72 percent / NaOMe / methanol

3: p-TsOH

4: 93 percent / NaH; TBAI / dimethylformamide

With sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; silver carbonate; toluene-4-sulfonic acid; In methanol; N,N-dimethyl-formamide;
DOI:10.1021/ja016227r