{(2S,3S,4S,6S)-3-Benzyloxy-6-[(2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(2,6-dimethoxy-phenoxy)-tetrahydro-pyran-3-yloxy]-2,4-dimethyl-tetrahydro-pyran-4-yl}-carbamic acid benzyl ester

Base Information

• Chemical Name: {(2S,3S,4S,6S)-3-Benzyloxy-6-[(2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(2,6-dimethoxy-phenoxy)-tetrahydro-pyran-3-yloxy]-2,4-dimethyl-tetrahydro-pyran-4-yl}-carbamic acid benzyl ester
• CAS No.: 213681-60-8
• Molecular Formula: C₅₇H₆₃NO₁₂
• Molecular Weight: 954.127

Synonyms:{(2S,3S,4S,6S)-3-Benzyloxy-6-[(2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(2,6-dimethoxy-phenoxy)-tetrahydro-pyran-3-yloxy]-2,4-dimethyl-tetrahydro-pyran-4-yl}-carbamic acid benzyl ester

Chemical Property of {(2S,3S,4S,6S)-3-Benzyloxy-6-[(2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(2,6-dimethoxy-phenoxy)-tetrahydro-pyran-3-yloxy]-2,4-dimethyl-tetrahydro-pyran-4-yl}-carbamic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

Technology Process of {(2S,3S,4S,6S)-3-Benzyloxy-6-[(2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(2,6-dimethoxy-phenoxy)-tetrahydro-pyran-3-yloxy]-2,4-dimethyl-tetrahydro-pyran-4-yl}-carbamic acid benzyl ester

There total 15 articles about {(2S,3S,4S,6S)-3-Benzyloxy-6-[(2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(2,6-dimethoxy-phenoxy)-tetrahydro-pyran-3-yloxy]-2,4-dimethyl-tetrahydro-pyran-4-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:

2,6-dimethoxyphenyl 3,4,6-tri-O-benzyl-β-D-glucopyranoside (135192-43-7) + ((2S,3S,4S)-3-Benzyloxy-6-fluoro-2,4-dimethyl-tetrahydro-pyran-4-yl)-carbamic acid benzyl ester (213681-57-3) → {(2S,3S,4S,6S)-3-Benzyloxy-6-[(2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(2,6-dimethoxy-phenoxy)-tetrahydro-pyran-3-yloxy]-2,4-dimethyl-tetrahydro-pyran-4-yl}-carbamic acid benzyl ester (213681-60-8) + {(2S,3S,4S,6R)-3-Benzyloxy-6-[(2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(2,6-dimethoxy-phenoxy)-tetrahydro-pyran-3-yloxy]-2,4-dimethyl-tetrahydro-pyran-4-yl}-carbamic acid benzyl ester

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; boron trifluoride diethyl etherate; In dichloromethane; at -30 - 25 ℃; for 72h; Yield given. Yields of byproduct given;

DOI:10.1002/(SICI)1521-3773(19980803)37:13/14<1871::AID-ANIE1871>3.0.CO;2-1

Reference yield:

1,3-dimethoxy-2-hydroxy-benzene (91-10-1) → {(2S,3S,4S,6S)-3-Benzyloxy-6-[(2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(2,6-dimethoxy-phenoxy)-tetrahydro-pyran-3-yloxy]-2,4-dimethyl-tetrahydro-pyran-4-yl}-carbamic acid benzyl ester (213681-60-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / BF₃*Et₂O, molecular sieves 4 Angstroem / CH₂Cl₂ / 24 h / -30 - 25 °C

2: 90 percent / NaOH, H₂O / methanol / 3 h / 25 °C

3: BF₃*Et₂O, Me₃SiOTf, molecular sieves 4 Angstroem / CH₂Cl₂ / 72 h / -30 - 25 °C

With sodium hydroxide; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; boron trifluoride diethyl etherate; water; In methanol; dichloromethane;

DOI:10.1002/(SICI)1521-3773(19980803)37:13/14<1871::AID-ANIE1871>3.0.CO;2-1

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → {(2S,3S,4S,6S)-3-Benzyloxy-6-[(2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(2,6-dimethoxy-phenoxy)-tetrahydro-pyran-3-yloxy]-2,4-dimethyl-tetrahydro-pyran-4-yl}-carbamic acid benzyl ester (213681-60-8)

Guidance literature:

Multi-step reaction with 4 steps

1: Na₂CO₃ / tetrahydrofuran; H₂O / 0.5 h / 0 - 25 °C

2: 1.) O₃, 2.) Ph₃P / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) CH₂Cl₂, -78 to 25 deg C, 3 h

3: 85 percent / DAST / CH₂Cl₂ / 1 h

4: BF₃*Et₂O, Me₃SiOTf, molecular sieves 4 Angstroem / CH₂Cl₂ / 72 h / -30 - 25 °C

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; boron trifluoride diethyl etherate; sodium carbonate; ozone; triphenylphosphine; 4,4'-diaminostilbene-2,2'-disulfonic acid; In tetrahydrofuran; dichloromethane; water;

DOI:10.1002/(SICI)1521-3773(19980803)37:13/14<1871::AID-ANIE1871>3.0.CO;2-1

upstream raw materials:

2,6-dimethoxyphenyl 3,4,6-tri-O-benzyl-β-D-glucopyranoside

((2S,3S,4S)-3-Benzyloxy-6-fluoro-2,4-dimethyl-tetrahydro-pyran-4-yl)-carbamic acid benzyl ester

1,3-dimethoxy-2-hydroxy-benzene

benzyl chloroformate

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