ethyl O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1→3)-4,6-O-benzylidene-2-deoxy-2-N-phthalimido-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: ethyl O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1→3)-4,6-O-benzylidene-2-deoxy-2-N-phthalimido-1-thio-β-D-glucopyranoside
• CAS No.: 1421193-35-2
• Molecular Formula: C₅₇H₅₇NO₁₁S
• Molecular Weight: 964.146
• Mol file: 1421193-35-2.mol

Synonyms:ethyl O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1→3)-4,6-O-benzylidene-2-deoxy-2-N-phthalimido-1-thio-β-D-glucopyranoside

Chemical Property of ethyl O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1→3)-4,6-O-benzylidene-2-deoxy-2-N-phthalimido-1-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1→3)-4,6-O-benzylidene-2-deoxy-2-N-phthalimido-1-thio-β-D-glucopyranoside

There total 3 articles about ethyl O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1→3)-4,6-O-benzylidene-2-deoxy-2-N-phthalimido-1-thio-β-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: 80.0%

(2R,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-chloro-tetrahydro-pyran (4291-68-3,25320-59-6,41110-63-8,67068-83-1,67773-44-8,69237-96-3,92470-93-4,93601-69-5,113829-62-2) + ethyl 4,6-O-benzylidene-2-deoxy-2-N-phthalamido-1-thio-β-Dglucopyranoside (99409-33-3) → ethyl O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1→3)-4,6-O-benzylidene-2-deoxy-2-N-phthalimido-1-thio-β-D-glucopyranoside (1421193-35-2)

Guidance literature:

With tetrabutylammomium bromide; N-ethyl-N,N-diisopropylamine; triethyl phosphite; In neat (no solvent); at 90 ℃; for 3h; stereoselective reaction;

DOI:10.1039/d0ob01024c

Reference yield: 74.0%

ethyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside (125411-99-6) + ethyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-N-phthalamido-1-thio-β-D-glucopyranoside (123212-53-3) → ethyl O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1→3)-4,6-O-benzylidene-2-deoxy-2-N-phthalimido-1-thio-β-D-glucopyranoside (1421193-35-2)

Guidance literature:

With N-iodo-succinimide; perchloric acid; silica gel; In diethyl ether; dichloromethane; at -25 ℃; for 1h; stereoselective reaction; Molecular sieve;

DOI:10.3762/bjoc.8.230

Reference yield: 74.0%

ethyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside (125411-99-6) + ethyl 4,6-O-benzylidene-2-deoxy-2-N-phthalamido-1-thio-β-Dglucopyranoside (99409-33-3) → ethyl O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1→3)-4,6-O-benzylidene-2-deoxy-2-N-phthalimido-1-thio-β-D-glucopyranoside (1421193-35-2)

Guidance literature:

With N-iodo-succinimide; In diethyl ether; dichloromethane; at -25 ℃; for 1h; stereoselective reaction; Molecular sieve;

DOI:10.3762/bjoc.8.230

upstream raw materials:

ethyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside

ethyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-N-phthalamido-1-thio-β-D-glucopyranoside

ethyl 4,6-O-benzylidene-2-deoxy-2-N-phthalamido-1-thio-β-Dglucopyranoside

(2R,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-chloro-tetrahydro-pyran

Downstream raw materials:

2-azidoethyl O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1→3)-O-(4,6-O-benzylidene-2-deoxy-2-N-phthalimido-β-D-glucopyranosyl)-(1→2)-O-(6-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1→4)-2,3,6-tri-O-benzyl-β-D-mannopyranoside