[(3S,4S,6S)-4-Benzyloxy-6-((2R,3R,4S,5R,6R)-4,5,6-tris-benzyloxy-3-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-yl]-methyl-carbamic acid 2-trimethylsilanyl-ethyl ester

Base Information

• Chemical Name: [(3S,4S,6S)-4-Benzyloxy-6-((2R,3R,4S,5R,6R)-4,5,6-tris-benzyloxy-3-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-yl]-methyl-carbamic acid 2-trimethylsilanyl-ethyl ester
• CAS No.: 309758-14-3
• Molecular Formula: C₄₇H₆₁NO₁₀Si
• Molecular Weight: 828.088

Synonyms:[(3S,4S,6S)-4-Benzyloxy-6-((2R,3R,4S,5R,6R)-4,5,6-tris-benzyloxy-3-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-yl]-methyl-carbamic acid 2-trimethylsilanyl-ethyl ester

Chemical Property of [(3S,4S,6S)-4-Benzyloxy-6-((2R,3R,4S,5R,6R)-4,5,6-tris-benzyloxy-3-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-yl]-methyl-carbamic acid 2-trimethylsilanyl-ethyl ester

Chemical Property:

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Technology Process of [(3S,4S,6S)-4-Benzyloxy-6-((2R,3R,4S,5R,6R)-4,5,6-tris-benzyloxy-3-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-yl]-methyl-carbamic acid 2-trimethylsilanyl-ethyl ester

There total 11 articles about [(3S,4S,6S)-4-Benzyloxy-6-((2R,3R,4S,5R,6R)-4,5,6-tris-benzyloxy-3-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-yl]-methyl-carbamic acid 2-trimethylsilanyl-ethyl 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: 93.0%

2-(Trimethylsilyl)ethyl 4-nitrophenyl carbonate (80149-80-0) + benzyl-O-[3-O-benzyl-4-methylamino-2,4-dideoxy-β-L-xylopyranosyl]-(1->6)-2,3-di-O-benzyl-4-O-methyl-β-D-glucopyranoside (309758-13-2) → [(3S,4S,6S)-4-Benzyloxy-6-((2R,3R,4S,5R,6R)-4,5,6-tris-benzyloxy-3-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-yl]-methyl-carbamic acid 2-trimethylsilanyl-ethyl ester (309758-14-3)

Guidance literature:

With 1-methyl-pyrrolidin-2-one; dmap; at 75 ℃; for 3h;

DOI:10.1021/jo000911r

Reference yield:

benzyl bromide (100-39-0) → [(3S,4S,6S)-4-Benzyloxy-6-((2R,3R,4S,5R,6R)-4,5,6-tris-benzyloxy-3-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-yl]-methyl-carbamic acid 2-trimethylsilanyl-ethyl ester (309758-14-3)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 80 percent / NaH / dimethylformamide / 1.5 h

2.1: OsO₄; NMO / acetone; 2-methyl-propan-2-ol / 2 h

3.1: 1.22 g / tetrahydrofuran; H₂O / 1 h

4.1: 81 percent / TsOH*H₂O / dioxane; H₂O / 21 h / 20 °C

5.1: 89 percent / DAST; 4A MS / tetrahydrofuran / 20 h / -78 °C

6.1: AgClO₄; SnCl₂; 4A MS / tetrahydrofuran / 6 h / -78 - -15 °C

6.2: 35 percent / LiAlH₄ / tetrahydrofuran / 1 h / Heating

7.1: 93 percent / DMAP; NMP / 3 h / 75 °C

With 1-methyl-pyrrolidin-2-one; dmap; osmium(VIII) oxide; N-methyl-2-indolinone; silver perchlorate; sodium hydride; toluene-4-sulfonic acid; 4,4'-diaminostilbene-2,2'-disulfonic acid; tin(ll) chloride; In tetrahydrofuran; 1,4-dioxane; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; 1.1: Alkylation / 2.1: dihydroxylation / 3.1: Oxidation / 4.1: Hydrolysis / 5.1: Substitution / 6.1: glycosulation / 6.2: Reduction / 7.1: Acylation;

DOI:10.1021/jo000911r

Reference yield:

4-O-methyl-1,2,3-O-benzyl-β-D-glucopyranoside (63629-66-3) → [(3S,4S,6S)-4-Benzyloxy-6-((2R,3R,4S,5R,6R)-4,5,6-tris-benzyloxy-3-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-yl]-methyl-carbamic acid 2-trimethylsilanyl-ethyl ester (309758-14-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: AgClO₄; SnCl₂; 4A MS / tetrahydrofuran / 6 h / -78 - -15 °C

1.2: 35 percent / LiAlH₄ / tetrahydrofuran / 1 h / Heating

2.1: 93 percent / DMAP; NMP / 3 h / 75 °C

With 1-methyl-pyrrolidin-2-one; dmap; silver perchlorate; tin(ll) chloride; In tetrahydrofuran; 1.1: glycosulation / 1.2: Reduction / 2.1: Acylation;

DOI:10.1021/jo000911r

upstream raw materials:

2-(Trimethylsilyl)ethyl 4-nitrophenyl carbonate

benzyl-O-[3-O-benzyl-4-methylamino-2,4-dideoxy-β-L-xylopyranosyl]-(1->6)-2,3-di-O-benzyl-4-O-methyl-β-D-glucopyranoside

benzyl bromide

4-O-methyl-1,2,3-O-benzyl-β-D-glucopyranoside

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