(4R,5R)-4-(benzyloxymethyl)-5-(1,3-dithian-2-ylmethyl)-2,2-dimethyl-1,3-dioxolane

Base Information

Chemical Name:(4R,5R)-4-(benzyloxymethyl)-5-(1,3-dithian-2-ylmethyl)-2,2-dimethyl-1,3-dioxolane
CAS No.:872831-93-1
Molecular Formula:C₁₈H₂₆O₃S₂
Molecular Weight:354.535
Hs Code.:

Synonyms:(4R,5R)-4-(benzyloxymethyl)-5-(1,3-dithian-2-ylmethyl)-2,2-dimethyl-1,3-dioxolane

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Chemical Property of (4R,5R)-4-(benzyloxymethyl)-5-(1,3-dithian-2-ylmethyl)-2,2-dimethyl-1,3-dioxolane

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Technology Process of (4R,5R)-4-(benzyloxymethyl)-5-(1,3-dithian-2-ylmethyl)-2,2-dimethyl-1,3-dioxolane

There total 2 articles about (4R,5R)-4-(benzyloxymethyl)-5-(1,3-dithian-2-ylmethyl)-2,2-dimethyl-1,3-dioxolane 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: 46.0%

: 505-23-7
1,3 dithiane

: 114826-50-5
(4R,5S)-4-((benzyloxy)methyl)-5-(iodomethyl)-2,2-dimethyl-1,3-dioxolane

: 872831-93-1
(4R,5R)-4-(benzyloxymethyl)-5-(1,3-dithian-2-ylmethyl)-2,2-dimethyl-1,3-dioxolane

Guidance literature:: 1,3 dithiane; With tert.-butyl lithium; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; at -78 ℃;

(4R,5S)-4-((benzyloxy)methyl)-5-(iodomethyl)-2,2-dimethyl-1,3-dioxolane; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; at -78 - 20 ℃; for 2h;
DOI:10.1021/jo0518093

Reference yield:

: 78469-77-9
1-O-benzyl-2,3-O-isopropylidene-D-threitol

: 872831-93-1
(4R,5R)-4-(benzyloxymethyl)-5-(1,3-dithian-2-ylmethyl)-2,2-dimethyl-1,3-dioxolane

Guidance literature:: Multi-step reaction with 2 steps

1.1: 98 percent / triphenylphosphine; I₂; imidazole / toluene / 0.33 h / Heating

2.1: t-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / -78 °C

2.2: 46 percent / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 2 h / -78 - 20 °C

With 1H-imidazole; iodine; tert.-butyl lithium; triphenylphosphine; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; toluene;
DOI:10.1021/jo0518093

Reference yield: 87.0%

: 872831-93-1
(4R,5R)-4-(benzyloxymethyl)-5-(1,3-dithian-2-ylmethyl)-2,2-dimethyl-1,3-dioxolane

: 74-88-4
methyl iodide

: 91526-98-6
benzyl (4R,5R)-2,2-dimethyl-5-(2-methyl-1,3-dithian-2-ylmethyl)-1,3-dioxolan-4-ylmethyl ether

Guidance literature:: (4R,5R)-4-(benzyloxymethyl)-5-(1,3-dithian-2-ylmethyl)-2,2-dimethyl-1,3-dioxolane; With tert.-butyl lithium; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; at -78 ℃;

methyl iodide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; at -78 ℃; for 1.5h;
DOI:10.1021/jo0518093