(1S,2R,3R,5R)-2-((benzyloxy)methyl)-6-oxabicyclo[3.1.0]hexan-3-yl methanesulfonate

Base Information

Chemical Name:(1S,2R,3R,5R)-2-((benzyloxy)methyl)-6-oxabicyclo[3.1.0]hexan-3-yl methanesulfonate
CAS No.:1353764-98-3
Molecular Formula:C₁₄H₁₈O₅S
Molecular Weight:298.36
Hs Code.:

Synonyms:(1S,2R,3R,5R)-2-((benzyloxy)methyl)-6-oxabicyclo[3.1.0]hexan-3-yl methanesulfonate

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Chemical Property of (1S,2R,3R,5R)-2-((benzyloxy)methyl)-6-oxabicyclo[3.1.0]hexan-3-yl methanesulfonate

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Technology Process of (1S,2R,3R,5R)-2-((benzyloxy)methyl)-6-oxabicyclo[3.1.0]hexan-3-yl methanesulfonate

There total 4 articles about (1S,2R,3R,5R)-2-((benzyloxy)methyl)-6-oxabicyclo[3.1.0]hexan-3-yl methanesulfonate 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: 61.0%

: 1146288-86-9
(1R,2S)-2-((benzyloxy)methyl)cyclopent-3-en-1-yl methanesulfonate

: 1353764-99-4
(1R,2R,3R,5S)-2-((benzyloxy)methyl)-6-oxabicyclo[3.1.0]hexan-3-yl methanesulfonate

: 1353764-98-3
(1S,2R,3R,5R)-2-((benzyloxy)methyl)-6-oxabicyclo[3.1.0]hexan-3-yl methanesulfonate

Guidance literature:: With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; water; at 0 - 20 ℃; for 24h; Inert atmosphere;
DOI:10.1021/ol203213f

Reference yield:

: 39939-07-6
5-(benzyloxymethyl)cyclopentadiene

: 1353764-99-4
(1R,2R,3R,5S)-2-((benzyloxy)methyl)-6-oxabicyclo[3.1.0]hexan-3-yl methanesulfonate

: 1353764-98-3
(1S,2R,3R,5R)-2-((benzyloxy)methyl)-6-oxabicyclo[3.1.0]hexan-3-yl methanesulfonate

Guidance literature:: Multi-step reaction with 3 steps

1.1: (+)-diisopinocampheylboron / tetrahydrofuran / -78 - -10 °C / Inert atmosphere

1.2: 24 h / 20 °C / Inert atmosphere

2.1: triethylamine / tetrahydrofuran / 0.67 h / 0 °C / Inert atmosphere

3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane; water / 24 h / 0 - 20 °C / Inert atmosphere

With (+)-diisopinocampheylboron; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; water;
DOI:10.1021/ol203213f

Reference yield:

: 3587-60-8
Benzyloxymethyl chloride

: 1353764-99-4
(1R,2R,3R,5S)-2-((benzyloxy)methyl)-6-oxabicyclo[3.1.0]hexan-3-yl methanesulfonate

: 1353764-98-3
(1S,2R,3R,5R)-2-((benzyloxy)methyl)-6-oxabicyclo[3.1.0]hexan-3-yl methanesulfonate

Guidance literature:: Multi-step reaction with 4 steps

1.1: tetrahydrofuran; N,N-dimethyl-formamide / 0.33 h / -40 °C / Inert atmosphere

2.1: (+)-diisopinocampheylboron / tetrahydrofuran / -78 - -10 °C / Inert atmosphere

2.2: 24 h / 20 °C / Inert atmosphere

3.1: triethylamine / tetrahydrofuran / 0.67 h / 0 °C / Inert atmosphere

4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane; water / 24 h / 0 - 20 °C / Inert atmosphere

With (+)-diisopinocampheylboron; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/ol203213f