(1R,4S,5R,7S)-3-benzyl-4-endo-methyl-7-endo-hydroxymethyl-6,8-dioxa-3-azabicyclo[3.2.1]octane

Base Information

Chemical Name:(1R,4S,5R,7S)-3-benzyl-4-endo-methyl-7-endo-hydroxymethyl-6,8-dioxa-3-azabicyclo[3.2.1]octane
CAS No.:250137-93-0
Molecular Formula:C₁₄H₁₉NO₃
Molecular Weight:249.31
Hs Code.:

Synonyms:(1R,4S,5R,7S)-3-benzyl-4-endo-methyl-7-endo-hydroxymethyl-6,8-dioxa-3-azabicyclo[3.2.1]octane

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Chemical Property of (1R,4S,5R,7S)-3-benzyl-4-endo-methyl-7-endo-hydroxymethyl-6,8-dioxa-3-azabicyclo[3.2.1]octane

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Technology Process of (1R,4S,5R,7S)-3-benzyl-4-endo-methyl-7-endo-hydroxymethyl-6,8-dioxa-3-azabicyclo[3.2.1]octane

There total 4 articles about (1R,4S,5R,7S)-3-benzyl-4-endo-methyl-7-endo-hydroxymethyl-6,8-dioxa-3-azabicyclo[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: 62.0%

: 250137-87-2
methyl (1S,4S,5R,7R)-3-benzyl-2-oxo-4-endo-methyl-6,8-dioxa-3-azabicyclo[3.2.1]octane-7-endo-carboxylate

: 250137-93-0
(1R,4S,5R,7S)-3-benzyl-4-endo-methyl-7-endo-hydroxymethyl-6,8-dioxa-3-azabicyclo[3.2.1]octane

Guidance literature:: With lithium aluminium tetrahydride; In tetrahydrofuran; for 2h; Heating;
DOI:10.1021/jo9904967

Reference yield:

: 6940-80-3,6940-81-4
(S)-N-benzylalaninol

: 250137-93-0
(1R,4S,5R,7S)-3-benzyl-4-endo-methyl-7-endo-hydroxymethyl-6,8-dioxa-3-azabicyclo[3.2.1]octane

Guidance literature:: Multi-step reaction with 4 steps

1: 69 percent / bromotripyrrolidinophosphonium hexafluorophosphate; DIPEA / CH₂Cl₂ / 12 h / 25 °C

2: 60 percent / (COCl)2; DMSO / CH₂Cl₂ / 0.25 h / -60 °C

3: H₂SO₄*SiO₂ / toluene / 0.33 h / Heating

4: 62 percent / LiAlH₄ / tetrahydrofuran / 2 h / Heating

With lithium aluminium tetrahydride; oxalyl dichloride; sulfuric acid; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; In tetrahydrofuran; dichloromethane; toluene; 1: Acylation / 2: Oxidation / 3: Cyclization / 4: Reduction;
DOI:10.1021/jo9904967

Reference yield:

: 250137-72-5
N-benzyl-N'-[(1S)-2-hydroxy-1-methylethyl]-(2R,3S)/(2S,3R)-2,3-di-isopropylidenetartramic acid methyl ester

: 250137-93-0
(1R,4S,5R,7S)-3-benzyl-4-endo-methyl-7-endo-hydroxymethyl-6,8-dioxa-3-azabicyclo[3.2.1]octane

Guidance literature:: Multi-step reaction with 3 steps

1: 60 percent / (COCl)2; DMSO / CH₂Cl₂ / 0.25 h / -60 °C

2: H₂SO₄*SiO₂ / toluene / 0.33 h / Heating

3: 62 percent / LiAlH₄ / tetrahydrofuran / 2 h / Heating

With lithium aluminium tetrahydride; oxalyl dichloride; sulfuric acid; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; toluene; 1: Oxidation / 2: Cyclization / 3: Reduction;
DOI:10.1021/jo9904967