trimethyl-[[(2R,3S,4S,5R,6R)-3,4,5,6-tetrakis(trimethylsilyloxy)oxan-2-yl]methoxy]silane

Base Information

• Chemical Name: trimethyl-[[(2R,3S,4S,5R,6R)-3,4,5,6-tetrakis(trimethylsilyloxy)oxan-2-yl]methoxy]silane
• CAS No.: 32166-80-6
• Molecular Formula: C₂₁H₅₂O₆Si₅
• Molecular Weight: 541.068
• DSSTox Substance ID: DTXSID60423817
• Nikkaji Number: J123.140E
• Wikidata: Q82236117
• Mol file: 32166-80-6.mol

Synonyms:32166-80-6;alpha-Galactose, TMS;.alpha.-Galactose, TMS;1,2,3,4,6-PENTA-O-TRIMETHYLSILYL-ALPHA-D-GALACTOPYRANOSE;trimethyl-[[(2R,3S,4S,5R,6R)-3,4,5,6-tetrakis(trimethylsilyloxy)oxan-2-yl]methoxy]silane;1,2,3,4,6-Pentakis-O-(trimethylsilyl) alpha-D-Galactose;19126-99-9;.alpha.-Galactopyranose, (5TMS);.alpha.-D-Galactopyranose, 1,2,3,4,6-pentakis-O-(trimethylsilyl)-;Galactopyranose, 1,2,3,4,6-pentakis-O-(trimethylsilyl)-, .alpha.-D-;.alpha.-D-Glactopyranose, 5TMS derivative;1,2,3,4,6-Pentakis-O-(trimethylsilyl)-.alpha.-D-Galactopyranose;SCHEMBL2521899;DTXSID60423817;PPFHNIVPOLWPCF-XDWAVFMPSA-N;1,2,3,4,6-Penta-O-trimethylsilyl alpha -D-galactose;1,2,3,4,6-Pentakis-O-(trimethylsilyl) ?-D-Galactose;1-O,2-O,3-O,4-O,6-O-Pentakis(trimethylsilyl)-alpha-D-galactopyranose

Chemical Property of trimethyl-[[(2R,3S,4S,5R,6R)-3,4,5,6-tetrakis(trimethylsilyloxy)oxan-2-yl]methoxy]silane

Chemical Property:

• PSA: 55.38000
• LogP: 6.07460
• Storage Temp.: 2-8°C
• Solubility.: Chloroform, Ethyl Acetate
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 11
• Exact Mass: 540.26102205
• Heavy Atom Count: 32
• Complexity: 586

Purity/Quality:

97% ^*data from raw suppliers

1,2,3,4,6-Pentakis-O-(trimethylsilyl)α-D-Galactose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[Si](C)(C)OCC1C(C(C(C(O1)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C
• Isomeric SMILES: C[Si](C)(C)OC[C@@H]1[C@@H]([C@@H]([C@H]([C@H](O1)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C
• Uses: TRIMETHYLSILYL-D-PLUS-GALACTOSE is used in the synthesis of truncated analogues of the iNKT cell agonist, α-galactosyl ceramide (KRN7000). 1,2,3,4,6-Pentakis-O-(trimethylsilyl) α-D-Galactose is used in the synthesis of truncated analogues of the iNKT cell agonist, α-galactosyl ceramide (KRN7000).

Technology Process of trimethyl-[[(2R,3S,4S,5R,6R)-3,4,5,6-tetrakis(trimethylsilyloxy)oxan-2-yl]methoxy]silane

There total 74 articles about trimethyl-[[(2R,3S,4S,5R,6R)-3,4,5,6-tetrakis(trimethylsilyloxy)oxan-2-yl]methoxy]silane 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:

(22S,25S)-26-O-β-D-glucopyranosyl-22,25-epoxy-furost-5-ene-1β,3β,26-triol 1-O-α-L-rhamnopyranosyl-(1→2)-O-[β-D-xylopyranosyl-(1→3)]-β-D-glucopyranoside + 1-(Trimethylsilyl)imidazole (18156-74-6) → D-xylose (6763-34-4) + alpha-D-glucopyranose (492-62-6) + 1,2,3,4,6-penta-O-trimethylsilyl-α-D-glucopyranose (1769-00-2,2775-90-8,3327-61-5,3411-25-4,19126-99-9,24707-99-1,24708-00-7,32166-80-6,32166-97-5,55057-23-3,55057-24-4,55057-25-5,55057-26-6,55521-15-8,55529-69-6,55529-70-9,122798-09-8,122798-11-2,122798-15-6,122798-16-7,122798-18-9,122798-19-0,143729-45-7) + 1,2,3,4-tetrakis-O-(trimethylsilyl)-α-D-xylopyranose (18622-98-5,18623-23-9,18623-24-0,18623-27-3,18771-81-8,20585-61-9,32166-72-6,32166-73-7,55555-45-8,56271-64-8,56271-65-9,56271-66-0,56271-67-1,56271-70-6,94942-10-6,14251-20-8) + 1,2,3,4-tetra-O-trimethysilyl-α-L-rhamnose (6778-50-3,32727-30-3,32727-31-4,55057-19-7,55057-20-0,55057-22-2,108392-01-4,55057-21-1) + L-rhamnose (6014-42-2)

Guidance literature:

(22S,25S)-26-O-β-D-glucopyranosyl-22,25-epoxy-furost-5-ene-1β,3β,26-triol 1-O-α-L-rhamnopyranosyl-(1→2)-O-[β-D-xylopyranosyl-(1→3)]-β-D-glucopyranoside; With hydrogenchloride; In water; at 90 ℃; for 3h;

1-(Trimethylsilyl)imidazole; In pyridine; at 50 ℃; for 0.5h;

DOI:10.1248/cpb.c16-00337

Reference yield:

3β-hydroxy-spirosta-5,25(27)-dien-1β-yl-O-α-L-rhamnopyranosyl-(1→2)-O-[β-D-xylopyranosyl-(1→3)]-β-D-glucopyranoside + 1-(Trimethylsilyl)imidazole (18156-74-6) → D-xylose (6763-34-4) + alpha-D-glucopyranose (492-62-6) + 1,2,3,4,6-penta-O-trimethylsilyl-α-D-glucopyranose (1769-00-2,2775-90-8,3327-61-5,3411-25-4,19126-99-9,24707-99-1,24708-00-7,32166-80-6,32166-97-5,55057-23-3,55057-24-4,55057-25-5,55057-26-6,55521-15-8,55529-69-6,55529-70-9,122798-09-8,122798-11-2,122798-15-6,122798-16-7,122798-18-9,122798-19-0,143729-45-7) + 1,2,3,4-tetrakis-O-(trimethylsilyl)-α-D-xylopyranose (18622-98-5,18623-23-9,18623-24-0,18623-27-3,18771-81-8,20585-61-9,32166-72-6,32166-73-7,55555-45-8,56271-64-8,56271-65-9,56271-66-0,56271-67-1,56271-70-6,94942-10-6,14251-20-8) + 1,2,3,4-tetra-O-trimethysilyl-α-L-rhamnose (6778-50-3,32727-30-3,32727-31-4,55057-19-7,55057-20-0,55057-22-2,108392-01-4,55057-21-1) + L-rhamnose (6014-42-2)

Guidance literature:

3β-hydroxy-spirosta-5,25(27)-dien-1β-yl-O-α-L-rhamnopyranosyl-(1→2)-O-[β-D-xylopyranosyl-(1→3)]-β-D-glucopyranoside; With hydrogenchloride; In water; at 90 ℃; for 3h;

1-(Trimethylsilyl)imidazole; In pyridine; at 50 ℃; for 0.5h;

DOI:10.1248/cpb.c16-00337

Reference yield:

3β-hydroxyspirosta-5,25(27)-dien-1β-yl-O-α-L-rhamnopyranosyl-(1→2)-O-[β-D-xylopyranosyl-(1→3)]-α-L-arabinopyranoside + 1-(Trimethylsilyl)imidazole (18156-74-6) → D-xylose (6763-34-4) + alpha-D-glucopyranose (492-62-6) + 1,2,3,4,6-penta-O-trimethylsilyl-α-D-glucopyranose (1769-00-2,2775-90-8,3327-61-5,3411-25-4,19126-99-9,24707-99-1,24708-00-7,32166-80-6,32166-97-5,55057-23-3,55057-24-4,55057-25-5,55057-26-6,55521-15-8,55529-69-6,55529-70-9,122798-09-8,122798-11-2,122798-15-6,122798-16-7,122798-18-9,122798-19-0,143729-45-7) + 1,2,3,4-tetrakis-O-(trimethylsilyl)-α-D-xylopyranose (18622-98-5,18623-23-9,18623-24-0,18623-27-3,18771-81-8,20585-61-9,32166-72-6,32166-73-7,55555-45-8,56271-64-8,56271-65-9,56271-66-0,56271-67-1,56271-70-6,94942-10-6,14251-20-8) + 1,2,3,4-tetra-O-trimethysilyl-α-L-rhamnose (6778-50-3,32727-30-3,32727-31-4,55057-19-7,55057-20-0,55057-22-2,108392-01-4,55057-21-1) + L-rhamnose (6014-42-2)

Guidance literature:

3β-hydroxyspirosta-5,25(27)-dien-1β-yl-O-α-L-rhamnopyranosyl-(1→2)-O-[β-D-xylopyranosyl-(1→3)]-α-L-arabinopyranoside; With hydrogenchloride; In water; at 90 ℃; for 3h;

1-(Trimethylsilyl)imidazole; In pyridine; at 50 ℃; for 0.5h;

DOI:10.1248/cpb.c16-00337

upstream raw materials:

chloro-trimethyl-silane

D-Galactose

1,1,1,3,3,3-hexamethyl-disilazane

D-Galactose

Downstream raw materials:

(2S,3S,4R)-1-O-(6-deoxy-6-phenylaminocarbonylamino-α-D-galactopyranosyl)-2-[(N-hexacosanoyl)amino]octadecane-3,4-diol

(2S,3S,4R)-1-O-(6-deoxy-6-acetamido-α-D-galactopyranosyl)-2-(N-nervonoylamino)-1,3,4-octadecanetriol

(2S,3S,4R)-2-azido-3,4-O-dibenzyl-1-O-α-D-galactopyranosyloctadec-6-ene-1,3,4-triol

C₅₀H₈₉N₃O₈Si₄

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