[(R)-2-[1-((2S,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-ylmethyl)-vinyloxy]-2-((R)-2,2-dimethyl-5-phenylsulfanyl-[1,3]dioxolan-4-yl)-ethoxy]-tert-butyl-diphenyl-silane

Base Information

• Chemical Name: [(R)-2-[1-((2S,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-ylmethyl)-vinyloxy]-2-((R)-2,2-dimethyl-5-phenylsulfanyl-[1,3]dioxolan-4-yl)-ethoxy]-tert-butyl-diphenyl-silane
• CAS No.: 652991-30-5
• Molecular Formula: C₆₀H₇₀O₉SSi
• Molecular Weight: 995.362

Synonyms:[(R)-2-[1-((2S,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-ylmethyl)-vinyloxy]-2-((R)-2,2-dimethyl-5-phenylsulfanyl-[1,3]dioxolan-4-yl)-ethoxy]-tert-butyl-diphenyl-silane

Chemical Property of [(R)-2-[1-((2S,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-ylmethyl)-vinyloxy]-2-((R)-2,2-dimethyl-5-phenylsulfanyl-[1,3]dioxolan-4-yl)-ethoxy]-tert-butyl-diphenyl-silane

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

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Useful:

Technology Process of [(R)-2-[1-((2S,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-ylmethyl)-vinyloxy]-2-((R)-2,2-dimethyl-5-phenylsulfanyl-[1,3]dioxolan-4-yl)-ethoxy]-tert-butyl-diphenyl-silane

There total 7 articles about [(R)-2-[1-((2S,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-ylmethyl)-vinyloxy]-2-((R)-2,2-dimethyl-5-phenylsulfanyl-[1,3]dioxolan-4-yl)-ethoxy]-tert-butyl-diphenyl-silane 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: 60.0%

((2S,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yl)-acetic acid (R)-2-(tert-butyl-diphenyl-silanyloxy)-1-((R)-2,2-dimethyl-5-phenylsulfanyl-[1,3]dioxolan-4-yl)-ethyl ester (652991-29-2) → [(R)-2-[1-((2S,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-ylmethyl)-vinyloxy]-2-((R)-2,2-dimethyl-5-phenylsulfanyl-[1,3]dioxolan-4-yl)-ethoxy]-tert-butyl-diphenyl-silane (652991-30-5)

Guidance literature:

With pyridine; In tetrahydrofuran; toluene; at -78 - 20 ℃;

DOI:10.1081/CAR-120026467

Reference yield:

5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribofuranose (96690-02-7) → [(R)-2-[1-((2S,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-ylmethyl)-vinyloxy]-2-((R)-2,2-dimethyl-5-phenylsulfanyl-[1,3]dioxolan-4-yl)-ethoxy]-tert-butyl-diphenyl-silane (652991-30-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 77 percent / I₂ / cyclohexane / 4 h / 20 °C

2: BF₃*Et₂O / CH₂Cl₂ / -78 - -40 °C

3: NaOMe / methanol / 0.5 h / 20 °C

4: 85 percent / DCC; DMAP / benzene / 0 - 20 °C

5: 60 percent / pyridine / tetrahydrofuran; toluene / -78 - 20 °C

With pyridine; dmap; boron trifluoride diethyl etherate; iodine; sodium methylate; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; dichloromethane; cyclohexane; toluene; benzene;

DOI:10.1081/CAR-120026467

Reference yield:

methyl (4S)-2,3,6-tri-O-benzyl-4-deoxy-4-(2-ethanoic acid)-α-D-glucopyranoside (224324-88-3) → [(R)-2-[1-((2S,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-ylmethyl)-vinyloxy]-2-((R)-2,2-dimethyl-5-phenylsulfanyl-[1,3]dioxolan-4-yl)-ethoxy]-tert-butyl-diphenyl-silane (652991-30-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / DCC; DMAP / benzene / 0 - 20 °C

2: 60 percent / pyridine / tetrahydrofuran; toluene / -78 - 20 °C

With pyridine; dmap; dicyclohexyl-carbodiimide; In tetrahydrofuran; toluene; benzene;

DOI:10.1081/CAR-120026467

upstream raw materials:

((2S,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yl)-acetic acid (R)-2-(tert-butyl-diphenyl-silanyloxy)-1-((R)-2,2-dimethyl-5-phenylsulfanyl-[1,3]dioxolan-4-yl)-ethyl ester

5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribofuranose

methyl (4S)-2,3,6-tri-O-benzyl-4-deoxy-4-(2-ethanoic acid)-α-D-glucopyranoside

4-O-tert-butyl(diphenyl)silyl-1,2-O-isopropylidene-D-erythro-S-phenyl monothiohemiacetal

Downstream raw materials:

methyl 4-C-(2,6-anhydro-7-O-tert-butyl(diphenyl)silyl-4,5-O-isopropylidene-1,3-dideoxy-D-ribo-hept-2-enitol-1-C-yl)-2,3,6-tri-O-benzyl-4-deoxy-α-D-glucopyranoside

methyl 4-C-(2,6-anhydro-1-deoxy-D-glycero-D-manno-heptitol-1-C-yl)-2,3,6-tri-O-benzyl-4-deoxy-α-D-glucopyranoside

methyl 4-C-(2,6-anhydro-7-O-tert-butyl(diphenyl)silyl-4,5-O-isopropylidene-1-deoxy-D-glycero-D-manno-heptitol-1-C-yl)-2,3,6-tri-O-benzyl-4-deoxy-α-D-glucopyranoside

methyl 4-C-(2,6-anhydro-7-O-tert-butyl(diphenyl)silyl-1-deoxy-D-glycero-D-manno-heptitol-1-C-yl)-2,3,6-tri-O-benzyl-4-deoxy-α-D-glucopyranoside

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