(1S,2S,3S,4R,6R)-2,3-Bis-benzyloxy-6-benzyloxymethyl-4-((2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-cyclohexanol

Base Information

Chemical Name:(1S,2S,3S,4R,6R)-2,3-Bis-benzyloxy-6-benzyloxymethyl-4-((2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-cyclohexanol
CAS No.:186820-78-0
Molecular Formula:C₅₆H₆₂O₁₀
Molecular Weight:895.102
Hs Code.:

(1S,2S,3S,4R,6R)-2,3-Bis-benzyloxy-6-benzyloxymethyl-4-((2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-cyclohexanol

Synonyms:(1S,2S,3S,4R,6R)-2,3-Bis-benzyloxy-6-benzyloxymethyl-4-((2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-cyclohexanol

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Chemical Property of (1S,2S,3S,4R,6R)-2,3-Bis-benzyloxy-6-benzyloxymethyl-4-((2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-cyclohexanol

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Technology Process of (1S,2S,3S,4R,6R)-2,3-Bis-benzyloxy-6-benzyloxymethyl-4-((2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-cyclohexanol

There total 9 articles about (1S,2S,3S,4R,6R)-2,3-Bis-benzyloxy-6-benzyloxymethyl-4-((2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-cyclohexanol 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: 54.0%

: 186820-77-9
(2R,3S,4R,6R)-2,3-Bis-benzyloxy-6-benzyloxymethyl-4-((2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-cyclohexanone

: 186820-78-0
(1S,2S,3S,4R,6R)-2,3-Bis-benzyloxy-6-benzyloxymethyl-4-((2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-cyclohexanol

Guidance literature:: With L-Selectride; In tetrahydrofuran; at 0 ℃; for 0.5h;
DOI:10.1002/(SICI)1099-0690(199806)1998:6<1099::AID-EJOC1099<3.0.CO;2-R

Reference yield:

: 100-39-0
benzyl bromide

: 186820-78-0
(1S,2S,3S,4R,6R)-2,3-Bis-benzyloxy-6-benzyloxymethyl-4-((2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-cyclohexanol

Guidance literature:: Multi-step reaction with 4 steps

1: 92 percent / NaH / dimethylformamide / 24 h / Ambient temperature

2: 1)BH₃*Me₃N, mol. sieves 4 Angstroem, 2) AlCl₃ / 1) THF, 30 min, RT, 2) THF, 2 h, RT

3: PCC, mol. sieves 4 Angstroem / CH₂Cl₂ / 3 h / Ambient temperature

4: 54 percent / L-selectride / tetrahydrofuran / 0.5 h / 0 °C

With aluminium trichloride; trimethylamine-borane; 4 A molecular sieve; L-Selectride; sodium hydride; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/(SICI)1099-0690(199806)1998:6<1099::AID-EJOC1099<3.0.CO;2-R

Reference yield:

: 19488-49-4
methyl 2,3,6-tri-O-benzyl-β-D-glucopyranoside

: 186820-78-0
(1S,2S,3S,4R,6R)-2,3-Bis-benzyloxy-6-benzyloxymethyl-4-((2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-cyclohexanol

Guidance literature:: Multi-step reaction with 8 steps

1: NaH, 15-crown-5 ether / 1) DMF, RT, 1 h, 2) DMF, 70 deg C, 3 h

2: 74 percent / DMSO, Ac₂O / 4 h / Ambient temperature

3: 58 percent / DBU / toluene / 0.33 h / 80 °C

4: 50 percent / NaBH₄, CeCl₃*7H₂O / methanol; CH₂Cl₂ / 0.5 h / Ambient temperature

5: 92 percent / NaH / dimethylformamide / 24 h / Ambient temperature

6: 1)BH₃*Me₃N, mol. sieves 4 Angstroem, 2) AlCl₃ / 1) THF, 30 min, RT, 2) THF, 2 h, RT

7: PCC, mol. sieves 4 Angstroem / CH₂Cl₂ / 3 h / Ambient temperature

8: 54 percent / L-selectride / tetrahydrofuran / 0.5 h / 0 °C

With sodium tetrahydroborate; aluminium trichloride; cerium(III) chloride; 15-crown-5; trimethylamine-borane; 4 A molecular sieve; acetic anhydride; L-Selectride; sodium hydride; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; pyridinium chlorochromate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1002/(SICI)1099-0690(199806)1998:6<1099::AID-EJOC1099<3.0.CO;2-R