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

Base Information

• Chemical Name: (2R,3R,4S,5R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-benzylsulfanyl-tetrahydro-pyran
• CAS No.: 217456-63-8
• Molecular Formula: C₄₁H₄₂O₅S
• Molecular Weight: 646.847

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

Chemical Property of (2R,3R,4S,5R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-benzylsulfanyl-tetrahydro-pyran

Chemical Property:

Purity/Quality:

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Technology Process of (2R,3R,4S,5R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-benzylsulfanyl-tetrahydro-pyran

There total 2 articles about (2R,3R,4S,5R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-benzylsulfanyl-tetrahydro-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:

methyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside (3879-79-6,17791-37-6,19488-61-0,53008-63-2,61330-62-9,69237-94-1,69237-95-2,71526-33-5,83462-67-3,84799-77-9,103421-29-0,103421-30-3,139241-42-2) → (2R,3R,4S,5R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-benzylsulfanyl-tetrahydro-pyran (217456-63-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 2M H₂SO₄ / acetic acid; H₂O

2: Me₃SiCl, Zn(OTf)2

With chloro-trimethyl-silane; sulfuric acid; zinc trifluoromethanesulfonate; In water; acetic acid;

DOI:10.1016/S0040-4039(98)01822-X

Reference yield:

2,3,4,6-Tetra-O-benzyl-D-glucopyranose (4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5,4132-28-9) + phenylmethanethiol (100-53-8) → (2R,3R,4S,5R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-benzylsulfanyl-tetrahydro-pyran (217456-63-8)

Guidance literature:

With chloro-trimethyl-silane; zinc trifluoromethanesulfonate;

DOI:10.1016/S0040-4039(98)01822-X

Reference yield: 95.0%

(2R,3R,4S,5R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-benzylsulfanyl-tetrahydro-pyran (217456-63-8) → benzyl S,S-dioxo-2,3,4,6-tetra-O-benzyl-1-thio-D-glucopyranoside (217456-68-3)

Guidance literature:

With MMPA;

DOI:10.1016/S0040-4039(98)01881-4

upstream raw materials:

2,3,4,6-Tetra-O-benzyl-D-glucopyranose

phenylmethanethiol

methyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside

Downstream raw materials:

benzyl S,S-dioxo-2,3,4,6-tetra-O-benzyl-1-thio-D-glucopyranoside

benzyl S,S-dioxo-2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside

benzyl S,S-dioxo-2,3,4,6-tetra-O-benzyl-1-thio-α-D-glucopyranoside

N-[6-((3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-hexyl]-terephthalamic acid

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