2(R)-<1-(benzyloxy)-2(S)-propyl>-3(R)-methyl-4(S)-(<(2-methoxyethoxy)methyl>oxy)-6-methylenetetrahydropyran

Base Information

Chemical Name:2(R)-<1-(benzyloxy)-2(S)-propyl>-3(R)-methyl-4(S)-(<(2-methoxyethoxy)methyl>oxy)-6-methylenetetrahydropyran
CAS No.:96056-06-3
Molecular Formula:C₂₁H₃₂O₅
Molecular Weight:364.482
Hs Code.:

Synonyms:2(R)-<1-(benzyloxy)-2(S)-propyl>-3(R)-methyl-4(S)-(<(2-methoxyethoxy)methyl>oxy)-6-methylenetetrahydropyran

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Chemical Property of 2(R)-<1-(benzyloxy)-2(S)-propyl>-3(R)-methyl-4(S)-(<(2-methoxyethoxy)methyl>oxy)-6-methylenetetrahydropyran

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Technology Process of 2(R)-<1-(benzyloxy)-2(S)-propyl>-3(R)-methyl-4(S)-(<(2-methoxyethoxy)methyl>oxy)-6-methylenetetrahydropyran

There total 12 articles about 2(R)-<1-(benzyloxy)-2(S)-propyl>-3(R)-methyl-4(S)-(<(2-methoxyethoxy)methyl>oxy)-6-methylenetetrahydropyran 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: 62.0%

: 100-39-0
benzyl bromide

: 96056-05-2
(5R,4S,6R)-4,6-dimethyl-7(S)-(<(2-methoxyethoxy)methyl>oxy)-1(S)-(bromomethyl)-2,9-dioxabicyclo<3.3.1>nonane

: (4S,5R,6R,7S)-6-Benzyloxy-4-(2-methoxy-ethoxymethoxy)-5,7-dimethyl-2-methylene-oxocane

: 96056-06-3
2(R)-<1-(benzyloxy)-2(S)-propyl>-3(R)-methyl-4(S)-(<(2-methoxyethoxy)methyl>oxy)-6-methylenetetrahydropyran

Guidance literature:: With n-butyllithium; Yield given. Multistep reaction; 1.) hexane, THF, -78 deg C, 3.5 h; 2.) HMPA, 3.5 h, room temp.;
DOI:10.1021/ja00297a037

Reference yield:

: ((1aS,1bR,4S,4aR,5aR)-1b,4-Dimethyl-hexahydro-2,5-dioxa-cyclopropa[a]pentalen-5a-yl)-methanol

: 96056-06-3
2(R)-<1-(benzyloxy)-2(S)-propyl>-3(R)-methyl-4(S)-(<(2-methoxyethoxy)methyl>oxy)-6-methylenetetrahydropyran

Guidance literature:: Multi-step reaction with 6 steps

1: HClO₄ (62percent) / acetonitrile / 0.5 h / Ambient temperature

2: 81 percent / pyridine; CH₂Cl₂ / 1 h / -20 °C

3: 93 percent / (n-Bu)4NBr / hexamethylphosphoric acid triamide / 9 h / 45 °C

4: 1.) BH₃; 2.) NaOH (10percent), H₂O₂ (30percent) / 1.) THF, 1 h, room temp; 2.) H₂O, 1 h 40 min, 55 deg C

5: 90 percent / (i-Pr)2NEt / CH₂Cl₂ / 10 h / Ambient temperature

6: 1.) n-BuLi / 1.) hexane, THF, -78 deg C, 3.5 h; 2.) HMPA, 3.5 h, room temp.

With sodium hydroxide; n-butyllithium; perchloric acid; borane; tetrabutylammomium bromide; dihydrogen peroxide; N-ethyl-N,N-diisopropylamine; In pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; acetonitrile;
DOI:10.1021/ja00297a037

Reference yield:

: 96056-18-7
(5R,4S,6R)-4,6-dimethyl-7(S)-hydroxy-1(S)-(bromomethyl)-2,9-dioxabicyclo<3.3.1>nonane

: 96056-06-3
2(R)-<1-(benzyloxy)-2(S)-propyl>-3(R)-methyl-4(S)-(<(2-methoxyethoxy)methyl>oxy)-6-methylenetetrahydropyran

Guidance literature:: Multi-step reaction with 2 steps

1: 90 percent / (i-Pr)2NEt / CH₂Cl₂ / 10 h / Ambient temperature

2: 1.) n-BuLi / 1.) hexane, THF, -78 deg C, 3.5 h; 2.) HMPA, 3.5 h, room temp.

With n-butyllithium; N-ethyl-N,N-diisopropylamine; In dichloromethane;
DOI:10.1021/ja00297a037