(1'R,2'R,3'R,4'S,5'R)-2-[(2',3',4',5'-bis-(di-O-isopropylidene))-6'-benzyloxy-3',4'-bis-(benzyloxymethyl)-1'-hydroxy-hexyl]-2-methyl-1,3-dithiane

Base Information

Chemical Name:(1'R,2'R,3'R,4'S,5'R)-2-[(2',3',4',5'-bis-(di-O-isopropylidene))-6'-benzyloxy-3',4'-bis-(benzyloxymethyl)-1'-hydroxy-hexyl]-2-methyl-1,3-dithiane
CAS No.:172790-42-0
Molecular Formula:C₄₀H₅₂O₈S₂
Molecular Weight:724.98
Hs Code.:

Synonyms:(1'R,2'R,3'R,4'S,5'R)-2-[(2',3',4',5'-bis-(di-O-isopropylidene))-6'-benzyloxy-3',4'-bis-(benzyloxymethyl)-1'-hydroxy-hexyl]-2-methyl-1,3-dithiane

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Chemical Property of (1'R,2'R,3'R,4'S,5'R)-2-[(2',3',4',5'-bis-(di-O-isopropylidene))-6'-benzyloxy-3',4'-bis-(benzyloxymethyl)-1'-hydroxy-hexyl]-2-methyl-1,3-dithiane

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Technology Process of (1'R,2'R,3'R,4'S,5'R)-2-[(2',3',4',5'-bis-(di-O-isopropylidene))-6'-benzyloxy-3',4'-bis-(benzyloxymethyl)-1'-hydroxy-hexyl]-2-methyl-1,3-dithiane

There total 9 articles about (1'R,2'R,3'R,4'S,5'R)-2-[(2',3',4',5'-bis-(di-O-isopropylidene))-6'-benzyloxy-3',4'-bis-(benzyloxymethyl)-1'-hydroxy-hexyl]-2-methyl-1,3-dithiane 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: 53.0%

: 27969-97-7
2-lithio-2-methyl-1,3-dithiane

: 172790-40-8
(2S,3R,4S,5R)-2,3,4,5-bis(di-O-isopropylidene)-6-benzyloxy-(3,4-bis(benzyloxymethyl))hexan-1-al

: 172790-42-0
(1'R,2'R,3'R,4'S,5'R)-2-[(2',3',4',5'-bis-(di-O-isopropylidene))-6'-benzyloxy-3',4'-bis-(benzyloxymethyl)-1'-hydroxy-hexyl]-2-methyl-1,3-dithiane

: (1'S,2'R,3'R,4'S,5'R)-2-[(2',3',4',5'-bis(di-O-isopropylidene))-6'-benzyloxy-3',4'-bis-(benzyloxymethyl)-1'-hydroxy-hexyl]-2-methyl-1,3-dithiane

Guidance literature:: In tetrahydrofuran; at -78 ℃; for 0.333333h;
DOI:10.1021/jo000700m

Reference yield:

: 6007-26-7
2-methyl-1,3-dithian

: 172790-40-8
(2S,3R,4S,5R)-2,3,4,5-bis(di-O-isopropylidene)-6-benzyloxy-(3,4-bis(benzyloxymethyl))hexan-1-al

: 172790-42-0
(1'R,2'R,3'R,4'S,5'R)-2-[(2',3',4',5'-bis-(di-O-isopropylidene))-6'-benzyloxy-3',4'-bis-(benzyloxymethyl)-1'-hydroxy-hexyl]-2-methyl-1,3-dithiane

: (1'S,2'R,3'R,4'S,5'R)-2-[(2',3',4',5'-bis(di-O-isopropylidene))-6'-benzyloxy-3',4'-bis-(benzyloxymethyl)-1'-hydroxy-hexyl]-2-methyl-1,3-dithiane

Guidance literature:: 2-methyl-1,3-dithian; With n-butyllithium; In tetrahydrofuran; hexane; at -20 ℃; for 1.5h;

(2S,3R,4S,5R)-2,3,4,5-bis(di-O-isopropylidene)-6-benzyloxy-(3,4-bis(benzyloxymethyl))hexan-1-al; In tetrahydrofuran; hexane; at -78 ℃; for 0.333333h; Further stages.;
DOI:10.1021/jo000700m

Reference yield:

: 4039-82-1
Benzyl propargyl ether

: 172790-42-0
(1'R,2'R,3'R,4'S,5'R)-2-[(2',3',4',5'-bis-(di-O-isopropylidene))-6'-benzyloxy-3',4'-bis-(benzyloxymethyl)-1'-hydroxy-hexyl]-2-methyl-1,3-dithiane

Guidance literature:: Multi-step reaction with 7 steps

1.1: n-butyl lithium / tetrahydrofuran; hexane / 1.42 h / -78 °C

1.2: 84 percent / hexane; tetrahydrofuran / 1.03 h / -78 - 0 °C

2.1: 95 percent / LiI; glacial acetic acid / 1.5 h / 70 °C

3.1: 87 percent / Cu(I) (2-thiophenecarboxylate) / 1-methyl-pyrrolidin-2-one / 0 - 20 °C

4.1: 94 percent / DIBAL-H / CH₂Cl₂ / -40 - -10 °C

6.1: (COCl)2; DMSO; NEt₃ / CH₂Cl₂ / 1.5 h / -78 °C

7.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -20 °C

7.2: tetrahydrofuran; hexane / 0.33 h / -78 °C

With n-butyllithium; oxalyl dichloride; copper(I) thiophene-2-carboxylate; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; triethylamine; lithium iodide; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; hexane; dichloromethane; 1.1: Metallation / 1.2: Substitution / 2.1: Addition / 3.1: Condensation / 4.1: Reduction / 6.1: Swern oxidation / 7.1: Metallation / 7.2: Substitution;
DOI:10.1021/jo000700m