(1S,2R,3S,4R,5R)-2-Allyl-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]octane

Base Information

Chemical Name:(1S,2R,3S,4R,5R)-2-Allyl-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]octane
CAS No.:138607-46-2
Molecular Formula:C₂₃H₂₆O₄
Molecular Weight:366.457
Hs Code.:

Synonyms:(1S,2R,3S,4R,5R)-2-Allyl-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]octane

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Chemical Property of (1S,2R,3S,4R,5R)-2-Allyl-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]octane

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Technology Process of (1S,2R,3S,4R,5R)-2-Allyl-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]octane

There total 2 articles about (1S,2R,3S,4R,5R)-2-Allyl-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]octane 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:

: 74878-90-3
Toluene-4-sulfonic acid (1S,2S,3S,4R,5R)-2-allyl-3-hydroxy-6,8-dioxa-bicyclo[3.2.1]oct-4-yl ester

: 138607-46-2
(1S,2R,3S,4R,5R)-2-Allyl-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]octane

Guidance literature:: Multi-step reaction with 2 steps

1: Na-Hg, methanol / 12 h / Ambient temperature

2: 1) NaH, 2) imidazole / n-Bu₄NI / 1) THF, DMF, 0 deg C, 30 min., 2) r.t., 24 h

With 1H-imidazole; methanol; sodium amalgam; sodium hydride; tetra-(n-butyl)ammonium iodide;
DOI:10.1021/jo00028a017

Reference yield:

: 100-39-0
benzyl bromide

: (1S,2S,3S,4R,5R)-2-Allyl-6,8-dioxa-bicyclo[3.2.1]octane-3,4-diol

: 138607-46-2
(1S,2R,3S,4R,5R)-2-Allyl-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]octane

Guidance literature:: With 1H-imidazole; sodium hydride; tetra-(n-butyl)ammonium iodide; Yield given. Multistep reaction; 1) THF, DMF, 0 deg C, 30 min., 2) r.t., 24 h;
DOI:10.1021/jo00028a017

Reference yield:

: 138607-46-2
(1S,2R,3S,4R,5R)-2-Allyl-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]octane

: (2R,3R,4R,5R)-4,5-Bis-benzyloxy-1-((1S,2R,3S,4R,5R)-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yl)-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-pentane-2,3-diol

Guidance literature:: Multi-step reaction with 8 steps

1: N-methylmorpholine N-oxide (NMMO), OsO₄ / acetone; H₂O / 6 h / Ambient temperature

2: NaIO₄ / methanol; H₂O / 2 h / Ambient temperature

3: NaBH₄ / methanol; diethyl ether / 1 h / 0 °C

4: 98 percent / Et₃N / diethyl ether / 3 h / 0 °C

5: 83 percent / NaI, NaHCO₃ / acetone / 12 h

6: 72 percent / dimethylformamide / 4 h / 110 °C

7: 1) n-BuLi / 1) THF, 0 deg C, 2) 0 deg C

8: 70 percent / N,N'-bis(mesitylmethyl)-(R,R')-1,2-diphenyl-1,2-diaminoethane / OsO₄ / CH₂Cl₂ / -80 °C

With sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; n-butyllithium; 1,2-diphenyl-N,N'-bis[(2,4,6-trimethylphenyl)methyl]-1,2-diaminoethane; sodium hydrogencarbonate; 4-methylmorpholine N-oxide; triethylamine; sodium iodide; osmium(VIII) oxide; In methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone;
DOI:10.1021/jo00028a017