(3S,4R,5R,6S)-3,4,5-Tris(benzyloxy)-2-(ethylthio)-6-methyltetrahydro-2H-pyran

Base Information

• Chemical Name: (3S,4R,5R,6S)-3,4,5-Tris(benzyloxy)-2-(ethylthio)-6-methyltetrahydro-2H-pyran
• CAS No.: 169532-17-6
• Molecular Formula: C₂₉H₃₄O₄S
• Molecular Weight: 478.653
• DSSTox Substance ID: DTXSID30454491
• Nikkaji Number: J790.252B
• Mol file: 169532-17-6.mol

Synonyms:169532-17-6;(3S,4R,5R,6S)-2-Ethylsulfanyl-6-methyl-3,4,5-tris(phenylmethoxy)oxane;(3S,4R,5R,6S)-3,4,5-Tris(benzyloxy)-2-(ethylthio)-6-methyltetrahydro-2H-pyran;116391-11-8;SCHEMBL2008597;DTXSID30454491;RZVKVTBAQRMTEH-JAGXECETSA-N;J-010554;2 3 4-TRI-O-BENZYL-1-S-ETHYL-BETA-L-THI&;Ethyl 2,3,4-Tri-O-benzyl-1-thio-alpha,beta-L-fucopyranoside;Ethyl 2-O,3-O,4-O-tribenzyl-6-deoxy-1-thio-L-galactopyranoside

Chemical Property of (3S,4R,5R,6S)-3,4,5-Tris(benzyloxy)-2-(ethylthio)-6-methyltetrahydro-2H-pyran

Chemical Property:

• Melting Point: >46°C (dec.)
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 5.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 11
• Exact Mass: 478.21778074
• Heavy Atom Count: 34
• Complexity: 542

Purity/Quality:

99%, ^*data from raw suppliers

Ethyl2,3,4-Tri-O-benzyl-1-thio-α,β-L-fucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCSC1C(C(C(C(O1)C)OCC2=CC=CC=C2)OCC3=CC=CC=C3)OCC4=CC=CC=C4
• Isomeric SMILES: CCSC1[C@H]([C@@H]([C@@H]([C@@H](O1)C)OCC2=CC=CC=C2)OCC3=CC=CC=C3)OCC4=CC=CC=C4
• Uses: Ethyl 2,3,4-Tri-O-benzyl-1-thio-α,-L-fucopyranoside is a useful reagent for the synthesis of oligosaccharides containing L-fucose.

Technology Process of (3S,4R,5R,6S)-3,4,5-Tris(benzyloxy)-2-(ethylthio)-6-methyltetrahydro-2H-pyran

There total 1 articles about (3S,4R,5R,6S)-3,4,5-Tris(benzyloxy)-2-(ethylthio)-6-methyltetrahydro-2H-pyran 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: 56.0%

→ ethyl 2,3,4-tri-O-benzyl-1-thio-α/β-L-fucopyranoside (169532-17-6,116391-11-8)

Guidance literature:

Reference yield: 83.0%

3-(benzyloxycarbonylamino)propyl 4-O-(6-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-6-O-t-butyldiphenylsilyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (1334630-73-7) + ethyl 2,3,4-tri-O-benzyl-1-thio-α/β-L-fucopyranoside (169532-17-6,116391-11-8) → 3-(benzyloxycarbonylamino)propyl O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1→2)-O-(6-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1→4)-6-O-t-butyldiphenylsilyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (1334630-94-2)

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; In toluene; at -30 ℃; for 2h; Molecular sieve; Inert atmosphere;

DOI:10.1007/s10719-015-9635-1

Reference yield: 81.0%

3-(benzyloxycarbonylamino)propyl 3-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranoside + ethyl 2,3,4-tri-O-benzyl-1-thio-α/β-L-fucopyranoside (169532-17-6,116391-11-8) → 3-(benzyloxycarbonylamino)propyl O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1→2)-3-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranoside

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; In dichloromethane; at -10 ℃; for 2h; stereoselective reaction; Molecular sieve; Inert atmosphere;

DOI:10.1007/s10719-015-9635-1

Downstream raw materials:

6-(N-benzyloxycarbonylamino)hexyl-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->3)-2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

perbenzyl fucosyl bromide

(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-Tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexanol

Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-2-[(2R,3R,4R,5S,6R)-3-acetylamino-2-azido-6-benzyloxymethyl-5-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester