(3aS,4R,6S,7R,7aS)-7-Benzyloxy-4-benzyloxymethyl-6-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran

Base Information

• Chemical Name: (3aS,4R,6S,7R,7aS)-7-Benzyloxy-4-benzyloxymethyl-6-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran
• CAS No.: 173029-45-3
• Molecular Formula: C₅₆H₆₀O₁₀S
• Molecular Weight: 925.152

Synonyms:(3aS,4R,6S,7R,7aS)-7-Benzyloxy-4-benzyloxymethyl-6-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran

Chemical Property of (3aS,4R,6S,7R,7aS)-7-Benzyloxy-4-benzyloxymethyl-6-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran

Chemical Property:

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Technology Process of (3aS,4R,6S,7R,7aS)-7-Benzyloxy-4-benzyloxymethyl-6-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran

There total 3 articles about (3aS,4R,6S,7R,7aS)-7-Benzyloxy-4-benzyloxymethyl-6-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran 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: 83.0%

benzyl bromide (100-39-0) + phenyl (3,4-di-O-isopropylidene-β-D-galactopyranosyl)-(1->4)-1-thio-β-D-glucopyranoside (173029-44-2) → (3aS,4R,6S,7R,7aS)-7-Benzyloxy-4-benzyloxymethyl-6-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran (173029-45-3)

Guidance literature:

With tetrabutylammomium bromide; sodium hydride; In N,N-dimethyl-formamide; 1.) 0 deg C, 1 h, 2.) RT, 12 h;

DOI:10.1248/cpb.43.1536

Reference yield:

thiophenol (108-98-5) → (3aS,4R,6S,7R,7aS)-7-Benzyloxy-4-benzyloxymethyl-6-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran (173029-45-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 88 percent / boron trifluoride etherate / CH₂Cl₂ / 24 h / Ambient temperature

2: 100 percent / NaOMe / methanol / 12 h / Ambient temperature

3: 67 percent / p-TsOH acid monohydrate / dimethylformamide / 48 h / 40 °C

4: 83 percent / NaH, n-Bu₄NBr / dimethylformamide / 1.) 0 deg C, 1 h, 2.) RT, 12 h

With boron trifluoride diethyl etherate; tetrabutylammomium bromide; sodium methylate; sodium hydride; toluene-4-sulfonic acid; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1248/cpb.43.1536

Reference yield:

1',2',3',6',2,3,4,6-octa-O-acetyl-β-D-lactose (3616-19-1,5328-50-7,5346-90-7,6291-42-5,6920-00-9,20764-63-0,20880-60-8,20880-65-3,22352-19-8,23973-20-8,32447-69-1,34213-32-6,52554-32-2,53956-64-2,56907-29-0,56994-12-8,56994-13-9,57128-38-8,67650-36-6,68036-17-9,68036-19-1,78215-50-6,78215-51-7,79549-48-7,80446-82-8,85249-04-3,93221-83-1,93779-27-2,111407-83-1,111407-84-2,111407-85-3,120328-65-6,123809-59-6,132341-46-9,132341-47-0,132341-49-2,145307-94-4) → (3aS,4R,6S,7R,7aS)-7-Benzyloxy-4-benzyloxymethyl-6-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran (173029-45-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 88 percent / boron trifluoride etherate / CH₂Cl₂ / 24 h / Ambient temperature

2: 100 percent / NaOMe / methanol / 12 h / Ambient temperature

3: 67 percent / p-TsOH acid monohydrate / dimethylformamide / 48 h / 40 °C

4: 83 percent / NaH, n-Bu₄NBr / dimethylformamide / 1.) 0 deg C, 1 h, 2.) RT, 12 h

With boron trifluoride diethyl etherate; tetrabutylammomium bromide; sodium methylate; sodium hydride; toluene-4-sulfonic acid; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1248/cpb.43.1536

upstream raw materials:

benzyl bromide

phenyl (3,4-di-O-isopropylidene-β-D-galactopyranosyl)-(1->4)-1-thio-β-D-glucopyranoside

thiophenol

1',2',3',6',2,3,4,6-octa-O-acetyl-β-D-lactose

Downstream raw materials:

N-trichloroethoxycarbonyl O-(2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1<*>4)-(2,3,6-tri-O-benzyl-β-D-glucopyranosyl)-L-serine benzyl ester

N-trichloroethoxycarbonyl O-(2,6-di-O-benzyl-β-D-galactopyranosyl)-(1<*>4)-(2,3,6-tri-O-benzyl-β-D-glucopyranosyl)-L-serine benzyl ester

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