(3S,4S,5R)-5-(2-(benzyloxy)ethyl)-4-hydroxy-5-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one

Base Information

Chemical Name:(3S,4S,5R)-5-(2-(benzyloxy)ethyl)-4-hydroxy-5-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one
CAS No.:1350524-15-0
Molecular Formula:C₁₅H₂₀O₅
Molecular Weight:280.321
Hs Code.:

Synonyms:(3S,4S,5R)-5-(2-(benzyloxy)ethyl)-4-hydroxy-5-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one

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Chemical Property of (3S,4S,5R)-5-(2-(benzyloxy)ethyl)-4-hydroxy-5-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one

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Technology Process of (3S,4S,5R)-5-(2-(benzyloxy)ethyl)-4-hydroxy-5-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one

There total 4 articles about (3S,4S,5R)-5-(2-(benzyloxy)ethyl)-4-hydroxy-5-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one 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:

: 5470-84-8
4-benzyloxybutanal

: 1350524-15-0
(3S,4S,5R)-5-(2-(benzyloxy)ethyl)-4-hydroxy-5-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one

: 5-(2-(benzyloxy)ethyl)-4-hydroxy-5-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one

: C₂₇H₃₅NO₇

Guidance literature:: Multi-step reaction with 3 steps

1: N,N-dimethylammonium chloride / water / 24 h / 70 °C / Inert atmosphere

2: dichloromethane / -78 °C / Inert atmosphere

3: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone / 24 h / Inert atmosphere

With osmium(VIII) oxide; N,N-dimethylammonium chloride; 4-methylmorpholine N-oxide; In dichloromethane; water; acetone;
DOI:10.1021/jo2021289

Reference yield:

: 4541-14-4
4-benzyloxy-butan-1-ol

: 1350524-15-0
(3S,4S,5R)-5-(2-(benzyloxy)ethyl)-4-hydroxy-5-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one

: 5-(2-(benzyloxy)ethyl)-4-hydroxy-5-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one

: C₂₇H₃₅NO₇

Guidance literature:: Multi-step reaction with 4 steps

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.25 h / -55 °C / Inert atmosphere

1.2: 0.25 h / -55 °C / Inert atmosphere

2.1: N,N-dimethylammonium chloride / water / 24 h / 70 °C / Inert atmosphere

3.1: dichloromethane / -78 °C / Inert atmosphere

4.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone / 24 h / Inert atmosphere

With osmium(VIII) oxide; oxalyl dichloride; N,N-dimethylammonium chloride; dimethyl sulfoxide; 4-methylmorpholine N-oxide; In dichloromethane; water; acetone;
DOI:10.1021/jo2021289

Reference yield:

: 1350524-09-2
(S)-4-benzyl-3-((2S,3S)-6-(benzyloxy)-3-hydroxy-2-methyl-4-methylenehexanoyl)-5,5-dimethyloxazolidin-2-one

: 1350524-15-0
(3S,4S,5R)-5-(2-(benzyloxy)ethyl)-4-hydroxy-5-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one

: 5-(2-(benzyloxy)ethyl)-4-hydroxy-5-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one

: C₂₇H₃₅NO₇

Guidance literature:: With osmium(VIII) oxide; 4-methylmorpholine N-oxide; In water; acetone; for 24h; optical yield given as %de; diastereoselective reaction; Inert atmosphere;
DOI:10.1021/jo2021289