(4aR,7R,7aS)-6-Allyloxy-7-benzyloxy-2,2-dimethyl-tetrahydro-furo[3,2-d][1,3]dioxine

Base Information

Chemical Name:(4aR,7R,7aS)-6-Allyloxy-7-benzyloxy-2,2-dimethyl-tetrahydro-furo[3,2-d][1,3]dioxine
CAS No.:916153-98-5
Molecular Formula:C₁₈H₂₄O₅
Molecular Weight:320.386
Hs Code.:

Synonyms:(4aR,7R,7aS)-6-Allyloxy-7-benzyloxy-2,2-dimethyl-tetrahydro-furo[3,2-d][1,3]dioxine

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Chemical Property of (4aR,7R,7aS)-6-Allyloxy-7-benzyloxy-2,2-dimethyl-tetrahydro-furo[3,2-d][1,3]dioxine

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Technology Process of (4aR,7R,7aS)-6-Allyloxy-7-benzyloxy-2,2-dimethyl-tetrahydro-furo[3,2-d][1,3]dioxine

There total 1 articles about (4aR,7R,7aS)-6-Allyloxy-7-benzyloxy-2,2-dimethyl-tetrahydro-furo[3,2-d][1,3]dioxine 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: 95.0%

: 100-39-0
benzyl bromide

: 916153-97-4
allyl 3,5-O-(1-methylethylidene)-α and β-D-xylofuranoside

: 916153-98-5
(4aR,7R,7aS)-6-Allyloxy-7-benzyloxy-2,2-dimethyl-tetrahydro-furo[3,2-d][1,3]dioxine

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; for 2h;
DOI:10.1021/jo0615504 DOI:10.1016/j.tetlet.2006.09.145

Reference yield: 84.0%

: 916153-98-5
(4aR,7R,7aS)-6-Allyloxy-7-benzyloxy-2,2-dimethyl-tetrahydro-furo[3,2-d][1,3]dioxine

: (3R,3aS,7aR)-3-(benzyloxy)-5,5-dimethyltetrahydro-2H-furo[3,2-d][1,3]dioxin-2-ol

Guidance literature:: (4aR,7R,7aS)-6-Allyloxy-7-benzyloxy-2,2-dimethyl-tetrahydro-furo[3,2-d][1,3]dioxine; With potassium tert-butylate; In dimethyl sulfoxide; at 80 ℃; for 0.25h;

With mercury(II) diacetate; In tetrahydrofuran; water; for 0.5h;
DOI:10.1021/jo0615504

Reference yield:

: 916153-98-5
(4aR,7R,7aS)-6-Allyloxy-7-benzyloxy-2,2-dimethyl-tetrahydro-furo[3,2-d][1,3]dioxine

: 6-benzyloxy-4-methoxy-12-methyl-oxacyclododec-7-ene-2,5-dione

Guidance literature:: Multi-step reaction with 12 steps

1.1: tBuOK / dimethylsulfoxide / 0.25 h / 80 °C

1.2: 84 percent / Hg(OAc)2 / tetrahydrofuran; H₂O / 0.5 h

2.1: 75 percent / nBuLi / tetrahydrofuran / 12 h / -50 - 20 °C

3.1: 96 percent / NaH / dimethylformamide / 2 h

4.1: 95 percent / TsOH*H₂O / methanol; H₂O / 3 h

5.1: 76 percent / iodine; PPh₃; imidazole / tetrahydrofuran / 12 h

6.1: methanol; H₂O / 12 h

6.2: 63 percent / aq. HCl / 6 h / 80 °C

7.1: 75 percent / TMSOTf / CH₂Cl₂ / 2 h

8.1: LiOH / tetrahydrofuran; H₂O / 12 h

9.1: 78 percent / 2,4,6-trichlorobenzoyl chloride; triethylamine; DMAP / tetrahydrofuran / 18 h

10.1: 93 percent / DDQ / CH₂Cl₂; H₂O / 2 h

11.1: 83 percent / Dess-Martin periodinane / CH₂Cl₂ / 3 h

12.1: PhCH=RuCl₂(PCy₃)2 / CH₂Cl₂ / 24 h / Heating

With 1H-imidazole; dmap; lithium hydroxide; n-butyllithium; trimethylsilyl trifluoromethanesulfonate; 2,4,6-trichlorobenzoyl chloride; potassium tert-butylate; iodine; sodium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; Grubbs catalyst first generation; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; 2.1: Wittig reaction / 9.1: Yamaguchi esterification;
DOI:10.1016/j.tetlet.2006.09.145