(3aS,4S,6R,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid (2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester

Base Information

• Chemical Name: (3aS,4S,6R,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid (2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester
• CAS No.: 74808-15-4
• Molecular Formula: C₄₃H₄₈O₁₁
• Molecular Weight: 740.848
• Mol file: 74808-15-4.mol

Synonyms:

Chemical Property of (3aS,4S,6R,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid (2S,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 (3aS,4S,6R,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid (2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester

There total 5 articles about (3aS,4S,6R,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid (2S,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: 66.0%

(3aS,4S,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylic acid (54622-95-6) + 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl trichloroacetimidate (74808-09-6) → (3aS,4S,6R,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid (2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester (74808-15-4)

Guidance literature:

In dichloromethane; at 20 ℃; for 4h;

Reference yield:

Cyclohexanecarboxylic acid (2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester (78890-57-0) → (3aS,4S,6R,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid (2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester (74808-15-4)

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) → (3aS,4S,6R,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid (2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester (74808-15-4)

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

upstream raw materials:

Methyl 2,3-O-isopropylidene-β-D-ribofuranuronosyl chloride

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

(3aS,4S,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylic acid

2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl trichloroacetimidate