(3aR,4R,6S,6aS)-4-Allyl-6-benzyloxy-4-methoxymethoxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole

Base Information

Chemical Name:(3aR,4R,6S,6aS)-4-Allyl-6-benzyloxy-4-methoxymethoxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole
CAS No.:161099-08-7
Molecular Formula:C₂₀H₂₈O₆
Molecular Weight:364.439
Hs Code.:

Synonyms:(3aR,4R,6S,6aS)-4-Allyl-6-benzyloxy-4-methoxymethoxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole

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Chemical Property of (3aR,4R,6S,6aS)-4-Allyl-6-benzyloxy-4-methoxymethoxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole

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Technology Process of (3aR,4R,6S,6aS)-4-Allyl-6-benzyloxy-4-methoxymethoxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole

There total 2 articles about (3aR,4R,6S,6aS)-4-Allyl-6-benzyloxy-4-methoxymethoxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole 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: 99.0%

: 107-30-2
chloromethyl methyl ether

: 158780-52-0
phenylmethyl 2,3-O-(1-methylethylidene)-4-C-(prop-2-enyl)-α-D-lyxofuranoside

: 161099-08-7
(3aR,4R,6S,6aS)-4-Allyl-6-benzyloxy-4-methoxymethoxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃;

Reference yield:

: 158780-50-8
(3aR,4S,6S,6aS)-4-Allyl-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methyl ester

: 161099-08-7
(3aR,4R,6S,6aS)-4-Allyl-6-benzyloxy-4-methoxymethoxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole

Guidance literature:: Multi-step reaction with 2 steps

1: 95 percent / LiAlH₄ / diethyl ether

2: 95 percent / iPr₂NEt / CH₂Cl₂

With lithium aluminium tetrahydride; N-ethyl-N,N-diisopropylamine; In diethyl ether; dichloromethane;
DOI:10.1016/S0040-4039(00)76001-1

Reference yield:

: 161099-08-7
(3aR,4R,6S,6aS)-4-Allyl-6-benzyloxy-4-methoxymethoxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole

: (1S,5R,6R,7R)-1-Allyl-6-benzyloxy-5-methoxymethoxymethyl-2,8-dioxa-bicyclo[3.2.1]octan-7-ol

Guidance literature:: Multi-step reaction with 12 steps

1: 1.) OsO₄, NMO; 2.) NaIO₄; 3.) NaBH₄ / 1.) THF, H₂O; 3.) EtOH

2: 98 percent / imidazole / dimethylformamide

3: Li / liquid ammonia

4: 1.) CCl₄; 2.) Li / 1.) HMPT, THF; 2.) liq. NH₃

5: NaH / dimethylformamide; tetrahydrofuran

6: 2,2-dimethyldioxirane / acetone; CH₂Cl₂ / 0 °C

7: 0.5 h / Ambient temperature

8: 76 percent / NaH / dimethylformamide; tetrahydrofuran

9: 1.) 1,4-diazabicyclo<2.2.2>octane; 2.) Hg(OAc)2 / 1.) (Ph₃P)3RhCl / 1.) EtOH, 2 h, reflux; 2.) THF, H₂O

10: 2.) Dess-Martin periodinane / 1.) THF

11: 89 percent / 50 percent HF / acetonitrile; H₂O / 2.5 h / Ambient temperature

12: DDQ / CH₂Cl₂; H₂O

With 1,4-diaza-bicyclo[2.2.2]octane; 1H-imidazole; tetrachloromethane; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; 2,2-dimethyldioxirane; hydrogen fluoride; mercury(II) diacetate; lithium; sodium hydride; Dess-Martin periodane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; Wilkinson's catalyst; In tetrahydrofuran; dichloromethane; ammonia; water; N,N-dimethyl-formamide; acetone; acetonitrile;
DOI:10.1016/S0040-4039(00)76001-1