Methyl 6-O-(tert-butyldiphenylsilyl)-alpha-D-glucopyranoside

Base Information

• Chemical Name: Methyl 6-O-(tert-butyldiphenylsilyl)-alpha-D-glucopyranoside
• CAS No.: 58479-62-2
• Molecular Formula: C₂₃H₃₂O₆Si
• Molecular Weight: 432.589
• DSSTox Substance ID: DTXSID501168375
• Nikkaji Number: J756.531C

Synonyms:SCHEMBL7901667;DTXSID501168375;Methyl 6-O-(tert-butyldiphenylsilyl)-alpha-D-glucopyranoside;Methyl 6-O-[(1,1-dimethylethyl)diphenylsilyl]-alpha-D-glucopyranoside

Chemical Property of Methyl 6-O-(tert-butyldiphenylsilyl)-alpha-D-glucopyranoside

Chemical Property:

• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 432.19681527
• Heavy Atom Count: 30
• Complexity: 508

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)[Si](C1=CC=CC=C1)(C2=CC=CC=C2)OCC3C(C(C(C(O3)OC)O)O)O
• Isomeric SMILES: CC(C)(C)[Si](C1=CC=CC=C1)(C2=CC=CC=C2)OC[C@@H]3[C@H]([C@@H]([C@H]([C@H](O3)OC)O)O)O

Technology Process of Methyl 6-O-(tert-butyldiphenylsilyl)-alpha-D-glucopyranoside

There total 5 articles about Methyl 6-O-(tert-butyldiphenylsilyl)-alpha-D-glucopyranoside 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: 98.0%

tert-butylchlorodiphenylsilane (58479-61-1) + methyl-alpha-D-glucopyranoside (97-30-3) → (2R,3S,4S,5R,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-methoxy-tetrahydro-pyran-3,4,5-triol (58479-62-2)

Guidance literature:

With dmap; triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

Reference yield: 98.0%

methyl 2,3,4-tri-O-benzyl-6-O-tert-butyldiphenylsilyl-α-D-glucopyranoside (58479-67-7) → (2R,3S,4S,5R,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-methoxy-tetrahydro-pyran-3,4,5-triol (58479-62-2)

Guidance literature:

With cyclohexene; palladium dihydroxide; In ethanol; for 2.5h; Heating;

DOI:10.1055/s-1981-29467

Reference yield: 63.0%

tert-butylchlorodiphenylsilane (58479-61-1) + methyl-alpha-D-glucopyranoside (97-30-3) → (2R,3S,4S,5R,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-methoxy-tetrahydro-pyran-3,4,5-triol (58479-62-2) + methyl 2,6-di-O-tert-butyldiphenylsilyl-α-D-glucopyranoside (488714-55-2)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 4 ℃; for 24h;

upstream raw materials:

methyl 2,3,4-tri-O-benzyl-6-O-tert-butyldiphenylsilyl-α-D-glucopyranoside

<2'R,2''R,6'R,6''R> methyl 6-O-(tert-butyldiphenylsilyl)-2-O,3-O-(6',6''-di-(2-oxoethyl)octahydro-2',2''-bipyran-2',2''-diyl)-α-D-glucopyranoside

tert-butylchlorodiphenylsilane

methyl-alpha-D-glucopyranoside

Downstream raw materials:

(3aR,4S,6R,7R,7aS)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-4-methoxy-2,2,2-triphenyl-tetrahydro-1,3,5-trioxa-2λ⁵-phospha-inden-7-ol

(3aR,4R,6S,7R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-6-methoxy-2,2,2-triphenyl-tetrahydro-1,3,5-trioxa-2λ⁵-phospha-inden-7-ol

<2'R,2''R,6'R,6''R> methyl 6-O-(tert-butyldiphenylsilyl)-2-O,3-O-(6',6''-diallyloctahydro-2',2''-bipyran-2',2''-diyl)-α-D-glucopyranoside

<2'R,2''R,6'R,6''R> methyl 4-O-acetyl-6-O-(tert-butyldiphenylsilyl)-2-O,3-O-(6',6''-diphenyloctahydro-2',2''-bipyran-2',2''-diyl)-α-D-glucopyranoside

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