Methoxy-acetic acid (2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester

Base Information

• Chemical Name: Methoxy-acetic acid (2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester
• CAS No.: 78890-59-2
• Molecular Formula: C₃₇H₄₀O₈
• Molecular Weight: 612.72
• Mol file: 78890-59-2.mol

Synonyms:Methoxy-acetic acid (2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester

Chemical Property of Methoxy-acetic acid (2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methoxy-acetic acid (2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester

There total 3 articles about Methoxy-acetic acid (2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-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:

Cyclohexanecarboxylic acid (2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester (78890-57-0) → Methoxy-acetic acid (2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester (78890-59-2)

Guidance literature:

Multi-step reaction with 2 steps

1: NaBH₄, BF₃*OEt₂ / bis-(2-methoxy-ethyl) ether / 1.) 0 deg C, 1 h, 2.) rt, 12 h

2: pyridine / 0 °C

With pyridine; sodium tetrahydroborate; boron trifluoride diethyl etherate; In diethylene glycol dimethyl ether;

DOI:10.1021/jo00336a034

Reference yield:

1-O-butanoyl-2,3,4,6-tetra-O-benzyl-α-D-glucopyranose (78890-54-7) → Methoxy-acetic acid (2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester (78890-59-2)

Guidance literature:

Multi-step reaction with 2 steps

1: NaBH₄, BF₃*OEt₂ / bis-(2-methoxy-ethyl) ether / 1.) 0 deg C, 1 h, 2.) rt, 20 h

2: pyridine / 0 °C

With pyridine; sodium tetrahydroborate; boron trifluoride diethyl etherate; In diethylene glycol dimethyl ether;

DOI:10.1021/jo00336a034

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) + Methoxyacetyl chloride (38870-89-2) → Methoxy-acetic acid (2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester (78890-59-2) + Methoxy-acetic acid (2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester (78890-60-5)

Guidance literature:

With pyridine; at 0 ℃; Yield given. Yields of byproduct given;

DOI:10.1021/jo00336a034

upstream raw materials:

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

Methoxyacetyl chloride

Cyclohexanecarboxylic acid (2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester

1-O-butanoyl-2,3,4,6-tetra-O-benzyl-α-D-glucopyranose

Downstream raw materials:

methyl 2,3,4-tri-O-benzyl-6-O-(2,3,4,6-tetra-O-benzyl-D-glucopyranosyl)-α-D-glucopyranoside

cholesteryl α- and β-2,3,4,6-tetra-O-benzyl-D-glucosides

phenyl 2,3,4,6-tetra-O-benzyl-1-thio-α/β-D-glucopyranoside

(1R)-<1-(2)H>-2,3,4,6-tetra-O-benzyl-1,5-anhydro-D-glucitol