Methanesulfonic acid (2R,3S,4R,5R,6S)-4,5-bis-benzyloxy-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Methanesulfonic acid (2R,3S,4R,5R,6S)-4,5-bis-benzyloxy-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-yl ester
• CAS No.: 74844-34-1
• Molecular Formula: C₂₂H₂₈O₈S
• Molecular Weight: 452.526

Synonyms:Methanesulfonic acid (2R,3S,4R,5R,6S)-4,5-bis-benzyloxy-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-yl ester

Chemical Property of Methanesulfonic acid (2R,3S,4R,5R,6S)-4,5-bis-benzyloxy-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-yl ester

Chemical Property:

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Technology Process of Methanesulfonic acid (2R,3S,4R,5R,6S)-4,5-bis-benzyloxy-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-yl ester

There total 3 articles about Methanesulfonic acid (2R,3S,4R,5R,6S)-4,5-bis-benzyloxy-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-yl ester 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-di-O-benzyl-4-O-mesyl-6-O-trityl-α-D-galactopyranoside (71756-39-3) → Methanesulfonic acid (2R,3S,4R,5R,6S)-4,5-bis-benzyloxy-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-yl ester (74844-34-1)

Guidance literature:

With water; acetic acid; at 100 ℃; for 4h;

DOI:10.1021/jo01310a060

Reference yield:

methyl 2,3-di-O-benzyl-α-D-galactopyranoside (29388-46-3) → Methanesulfonic acid (2R,3S,4R,5R,6S)-4,5-bis-benzyloxy-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-yl ester (74844-34-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) Pyridine, 75 deg C, 18 h; 2.) 0 deg C to room temperature, 2 days

2: 4:1 acetic acid, water / 4 h / 100 °C

With water; acetic acid;

DOI:10.1021/jo01310a060

Reference yield:

methyl 2,3-di-O-benzyl-4-O-(methylsulfonyl)-6-O-trityl-β-D-glucopyranoside (19877-37-3,20688-87-3,71756-39-3) → Methanesulfonic acid (2R,3R,4R,5R,6R)-4,5-bis-benzyloxy-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-yl ester (20688-89-5,74844-34-1,116013-34-4)

Guidance literature:

DOI:10.1016/S0008-6215(00)85562-7

upstream raw materials:

methyl 2,3-di-O-benzyl-4-O-mesyl-6-O-trityl-α-D-galactopyranoside

methyl 2,3-di-O-benzyl-α-D-galactopyranoside

methyl 2,3-di-O-benzyl-4-O-(methylsulfonyl)-6-O-trityl-β-D-glucopyranoside

Downstream raw materials:

methyl 4-azido-2,3-di-O-benzyl-4-deoxy-α-D-glucopyranoside

(2S,3S,4S,5R,6S)-3-Azido-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-2-carbaldehyde

2-((2S,3R,4S,5R,6S)-3-Azido-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-1,3-diphenyl-imidazolidine

N-{(2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-[(E)-(2S,3R,2'R)-2-([2,2']bi[1,4-dioxa-spiro[4.5]decyl]-3-yl)-vinyl]-6-methoxy-tetrahydro-pyran-3-yl}-acetamide

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