[(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-((2S,3R,4S,5R,6R)-3,4-bis-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-2-methoxy-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester

Base Information

• Chemical Name: [(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-((2S,3R,4S,5R,6R)-3,4-bis-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-2-methoxy-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester
• CAS No.: 122992-53-4
• Molecular Formula: C₄₉H₅₅NO₁₂
• Molecular Weight: 849.975

Synonyms:

Chemical Property of [(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-((2S,3R,4S,5R,6R)-3,4-bis-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-2-methoxy-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-((2S,3R,4S,5R,6R)-3,4-bis-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-2-methoxy-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester

There total 9 articles about [(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-((2S,3R,4S,5R,6R)-3,4-bis-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-2-methoxy-tetrahydro-pyran-3-yl]-carbamic acid benzyl 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: 99.0%

methyl 3,6-di-O-benzyl-2-(benzyloxycarbonylamino)-2-deoxy-4-O-(2,3-di-O-benzyl-4,6-O-isopropylidene-β-D-glucopyranosyl)-α-D-glucopyranoside (122992-52-3) → [(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-((2S,3R,4S,5R,6R)-3,4-bis-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-2-methoxy-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester (122992-53-4)

Guidance literature:

In water; acetic acid; for 16h; Ambient temperature;

Reference yield:

β-D-glucose pentaacetate (604-69-3) → [(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-((2S,3R,4S,5R,6R)-3,4-bis-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-2-methoxy-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester (122992-53-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 2-aminoethanol

3: 25 percent / boron trifluoride etherate / CH₂Cl₂ / polyethylene vessel!

4: 97 percent / potassium tert-butoxide / methanol; dioxane / 0.75 h / Ambient temperature

5: 97 percent / p-toluenesulphonic acid / dimethylformamide / 18 h / Ambient temperature

6: 66 percent / Ba(OH)2*8H₂O, BaO / dimethylformamide / 16 h / Ambient temperature

7: 99 percent / acetic acid; H₂O / 16 h / Ambient temperature

With barium dihydroxide; boron trifluoride diethyl etherate; toluene-4-sulfonic acid; ethanolamine; barium(II) oxide; potassium tert-butylate; In 1,4-dioxane; methanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide;

Reference yield:

2,3,4,5-tetra-O-acetyl-D-glucopyranose (3947-62-4,6207-76-7,19235-21-3,22554-70-7,22860-22-6,47339-09-3,57884-82-9,62057-79-8,70191-05-8,109525-54-4,140147-37-1,10343-06-3) → [(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-((2S,3R,4S,5R,6R)-3,4-bis-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-2-methoxy-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester (122992-53-4)

Guidance literature:

Multi-step reaction with 6 steps

2: 25 percent / boron trifluoride etherate / CH₂Cl₂ / polyethylene vessel!

3: 97 percent / potassium tert-butoxide / methanol; dioxane / 0.75 h / Ambient temperature

4: 97 percent / p-toluenesulphonic acid / dimethylformamide / 18 h / Ambient temperature

5: 66 percent / Ba(OH)2*8H₂O, BaO / dimethylformamide / 16 h / Ambient temperature

6: 99 percent / acetic acid; H₂O / 16 h / Ambient temperature

With barium dihydroxide; boron trifluoride diethyl etherate; toluene-4-sulfonic acid; barium(II) oxide; potassium tert-butylate; In 1,4-dioxane; methanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide;

upstream raw materials:

methyl 3,6-di-O-benzyl-2-(benzyloxycarbonylamino)-2-deoxy-4-O-(2,3-di-O-benzyl-4,6-O-isopropylidene-β-D-glucopyranosyl)-α-D-glucopyranoside

2,3,4,5-tetra-O-acetyl-D-glucopyranose

2,3,4,6-tetra-O-acetyl-d-glucopyranosyl trichloroacetimidate

methyl N-benzyloxycarbonyl-2-deoxy-3,6-di-O-benzylglucopyranoside

Downstream raw materials:

(2S,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-((2R,3S,4R,5R,6S)-4-benzyloxy-5-benzyloxycarbonylamino-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-3-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

methyl 3,6-di-O-benzyl-2-(benzyloxycarbonylamino)-2-deoxy-4-O-(2,3-di-O-benzyl-4-O-levulinoyl-β-D-glucopyranosyl)-α-D-glucopyranoside

methyl 3,6-di-O-benzyl-2-(benzyloxycarbonylamino)-2-deoxy-4-O-(methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronato)-α-D-glucopyranoside

((2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-{(2S,3R,4S,5R,6R)-3,4-bis-benzyloxy-6-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-hydroxy-tetrahydro-pyran-2-yloxy}-2-methoxy-tetrahydro-pyran-3-yl)-carbamic acid benzyl ester

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