(2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3-ol

Base Information

• Chemical Name: (2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3-ol
• CAS No.: 97974-20-4
• Molecular Formula: C₃₃H₃₄O₅S
• Molecular Weight: 542.696
• Mol file: 97974-20-4.mol

Synonyms:(2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3-ol

Chemical Property of (2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3-ol

Chemical Property:

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3-ol

There total 19 articles about (2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3-ol 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: 94.0%

S-phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thio-β-D-glucopyranoside (87470-70-0) → (2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3-ol (97974-20-4)

Guidance literature:

With hydrogenchloride; 4 A molecular sieve; sodium cyanoborohydride; In diethyl ether; at 0 ℃; for 0.25h;

DOI:10.1016/0008-6215(95)00203-6

Reference yield: 70.0%

S-phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thia-β-D-glucopyranoside (129171-17-1) → (2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3-ol (97974-20-4)

Guidance literature:

With sodium cyanoborohydride; In tetrahydrofuran;

DOI:10.1016/j.bmcl.2009.06.005

Reference yield: 62.0%

phenyl 4-O-benzoyl-2,3,6-tri-O-benzyl-1-thio-β-D-glucopyranoside → (2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3-ol (97974-20-4)

Guidance literature:

With sodium methylate; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1021/acs.joc.8b01459

upstream raw materials:

S-phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thio-β-D-glucopyranoside

(2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol

benzyl bromide

thiophenol

Downstream raw materials:

phenyl 2,3,6-tri-O-benzyl-4-deoxy-1-thio-β-D-xylo-hexopyranoside

2,3,6-tri-O-benzyl-4-deoxy-α-D-xylo-hexopyranosyl-(1->3)-2,4,6-tri-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl azide

2,3,6-tri-O-benzyl-4-deoxy-α-D-xylo-hexopyranosyl-(1->3)-2,4,6-tri-O-acetyl-β-D-galactopyranosyl-(1->4)-N-acetyl-2,3,6-tri-O-acetyl-β-D-glucopyranosylamine

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