(2R,3S,4R)-4-((tert-Butyldimethylsilyl)oxy)-2-(((tert-butyldimethylsilyl)oxy)methyl)-3,4-dihydro-2H-pyran-3-ol

Base Information

• Chemical Name: (2R,3S,4R)-4-((tert-Butyldimethylsilyl)oxy)-2-(((tert-butyldimethylsilyl)oxy)methyl)-3,4-dihydro-2H-pyran-3-ol
• CAS No.: 111902-03-5
• Molecular Formula: C18H38 O4 Si2
• Molecular Weight: 374.66
• DSSTox Substance ID: DTXSID40557008
• Wikidata: Q82438751
• Mol file: 111902-03-5.mol

Synonyms:111902-03-5;3,6-Di-O-(tert-butyldimethylsilyl)-D-galactal;(2R,3S,4R)-4-((tert-Butyldimethylsilyl)oxy)-2-(((tert-butyldimethylsilyl)oxy)methyl)-3,4-dihydro-2H-pyran-3-ol;3,6-Di-O-tert-butyldimethylsilyl-D-galactal;(2R,3S,4R)-4-[tert-butyl(dimethyl)silyl]oxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3,4-dihydro-2H-pyran-3-ol;DTXSID40557008;CS-0441200;3,6-Di-O-(tert-butyldimethylsilyl)-D-galactal, AldrichCPR;2,6-Anhydro-1,4-bis-O-[tert-butyl(dimethyl)silyl]-5-deoxy-D-arabino-hex-5-enitol

Chemical Property of (2R,3S,4R)-4-((tert-Butyldimethylsilyl)oxy)-2-(((tert-butyldimethylsilyl)oxy)methyl)-3,4-dihydro-2H-pyran-3-ol

Chemical Property:

• Refractive Index: n20/D 1.458(lit.)
• Boiling Point: 385.2°Cat760mmHg
• Flash Point: 186.8°C
• PSA: 47.92000
• Density: 0.96g/cm³
• LogP: 4.67200
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 374.23086276
• Heavy Atom Count: 24
• Complexity: 447

Purity/Quality:

95% ^*data from raw suppliers

3,6-Di-O-(tert-butyldimethylsilyl)-D-galactal Aldrich ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)[Si](C)(C)OCC1C(C(C=CO1)O[Si](C)(C)C(C)(C)C)O
• Isomeric SMILES: CC(C)(C)[Si](C)(C)OC[C@@H]1[C@@H]([C@@H](C=CO1)O[Si](C)(C)C(C)(C)C)O

Technology Process of (2R,3S,4R)-4-((tert-Butyldimethylsilyl)oxy)-2-(((tert-butyldimethylsilyl)oxy)methyl)-3,4-dihydro-2H-pyran-3-ol

There total 1 articles about (2R,3S,4R)-4-((tert-Butyldimethylsilyl)oxy)-2-(((tert-butyldimethylsilyl)oxy)methyl)-3,4-dihydro-2H-pyran-3-ol 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: 11.0%

tert-butyldimethylsilyl chloride (18162-48-6) + D-galactal (21193-75-9) → (2R,3R,4R)-2-(((tert-butyldimethylsilyl)oxy)methyl)-3,4-dihydro-2H-pyran-3,4-diol (124751-19-5) + 3,6-di-O-tert-butyldimethylsilyl-D-(-)-galactal (111902-03-5)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 0 ℃; for 0.666667h;

DOI:10.1016/0008-6215(90)84259-W

Reference yield: 86.0%

3,6-di-O-tert-butyldimethylsilyl-D-(-)-galactal (111902-03-5) + dibenzyl azodicarboxylate (2449-05-0) → <4aR-(4aα,6α,7α,8β,8aβ)>-8-<<(1,1-Dimethylethyl)dimethylsilyl>oxy>-6-<<<(1,1-dimethylethyl)dimethylsilyl>oxy>methyl>-4a,7,8,8a-tetrahydro-7-hydroxy-3-(phenylmethoxy)-1H,6H-pyrano<3,2-e><1,3,4>oxadiazine-1-carboxylic acid phenylmethyl ester (120120-69-6)

Guidance literature:

In dichloromethane; cyclohexane; Irradiation;

DOI:10.1021/ja00190a037

Reference yield: 85.0%

3,6-di-O-tert-butyldimethylsilyl-D-(-)-galactal (111902-03-5) + thiophenol (108-98-5) → C24H44O4SSi2

Guidance literature:

With oxotrichloro-triphenylphosphine-dimethylsulphoxide-rhenium(v); In toluene; at 23 ℃; for 3h;

DOI:10.1021/jacs.9b03982

upstream raw materials:

tert-butyldimethylsilyl chloride

D-galactal

Downstream raw materials:

(2R,3S,4R)-3-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,4-dihydro-2H-pyran

<4aR-(4aα,6α,7α,8β,8aβ)>-8-<<(1,1-Dimethylethyl)dimethylsilyl>oxy>-6-<<<(1,1-dimethylethyl)dimethylsilyl>oxy>methyl>-4a,7,8,8a-tetrahydro-7-hydroxy-3-(phenylmethoxy)-1H,6H-pyrano<3,2-e><1,3,4>oxadiazine-1-carboxylic acid phenylmethyl ester

4-O-Acetyl-1,5-anhydro-3,6-bis-O-(tert-butyldimethylsilyl)-2-deoxy-D-lyxo-hex-1-enitol

4-O-benzyl-D-(-)-galactal